How To Scale Customer Implementations

I’ve seen the evolution of customer implementations and onboarding at several B2B Saas companies and talked to many other Customer Success leaders in the industry.

Here are 3 common stages to understand and be prepared for.

3 Customer Onboarding Stages To Prep For

1. Implementation included with a month-to-month contract.

You’re a new kid on the scene.

Your goals:

• Get customers
• Make them wildly successful
• Learn a ton
• Build brand credibility and trust

This is the “Earn Their Business Every Month” playbook. It requires an emphasis on customer support, soliciting customer feedback, and quick product and customer experience iteration.  

It’s not going to be your long term business model but it’s a great place to start.

2. Paid implementations and annual contracts.

You have happy reference customers, some great success stories, and you’re known for your outstanding customer service. (Yay for investing in customer experience early on!)

Your industry has matured and annual contracts with paid implementations are the norm. High touch implementations delivered by your team are not cheap. You start charging. Other vendors have started this also and customers are used to the contract line item. You’re starting to get requests for custom integrations, additional training or strategy help, and other work outside of your implementation scope.

Your goals:

• Maintain an excellent customer experience
• Focus on financial predictability and stability - get cash up front, minimize cost centers
• Build a repeatable product planning and roll out process (it’s likely still messy)
• Continue to “templatize” your implementation process so it’s consistent and repeatable
• Test growth strategies like moving upmarket or into new geographies
• Turn your ad-hoc partners and consultants into an official partner program

3. Partner resellers and ecosystem.

Welcome to customer onboarding at scale! Partners handle most of the implementations and custom work. Many are also resellers. Their business is centered around providing strategy and consulting services for your industry and product. This works when demand is high, the market is big, and partners see the significant opportunity.  

Your goals:

• Equip partners to deliver excellent service through training, certifications, tools, and technical help
• Standardize partner contracts, financial incentives, and rules of engagement
• Build an internal department dedicated to partner support and development
• Consider product and technical strategy - do you enable an app ecosystem?

Salesforce is known for their partner programs. This or this could be you one day!

It’s Never One Size Fits All

Every business is different. If you serve enterprise customers, you’ll likely do annual contracts and (large!) paid implementations from Day 1. If you’re a product-led or freemium model, your goal may be to enable a fully automated onboarding.

These stages are a starting place for discussion and planning.

The goal is to deliver the best service, with a healthy business model, in the way that’s right for you and your customers!

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Here is my favorite customer success question to ask founders or leaders at a fast growing startup:

What do your users get measured on?

In other words, what is the one metric that is most important to their job success?

Examples of metrics that users care about:

• Revenue generated
• New leads
• Assets under management
• Website conversions
• Customer renewals
• Event attendees
• Customer satisfaction score
• Employee retention

Examples of typical customer success metrics:

• # of users
• # of logins
• Upgrade $
• Renewal $
• CSAT or NPS scores

Yes, those are helpful data points for the health of your business but your customers don’t care.

They care about doing their job better, hitting their metrics, and meeting their boss’s expectations.

How can you help your customer look like a rockstar?

If your team is optimizing for user activations or upgrade dollars, see if you can flip the internal conversation.

Steps to up-level customer success:

1. Identify the most important metric to your user.
2. Track that metric in your product (ideal) or gather manually (scrappy).
3. Make that your Customer Success North Star.
4. Talk about this North Start constantly within your company.
5. Create raving fans.
6. Grow an amazing business that changes the world! 🌎

HUGE SHOUT OUT to Francis Cordon, the ultimate Customer Success Sensei. He introduced me to this simple, brilliant, underutilized concept and I’ve been sharing it ever since. Thank you, Paco! 🙏🙏🙏

#always-be-testing Do you like this week’s O’Daily shortie? Or do you prefer longer form? I’d love to hear your thoughts!

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5 Interview Strategies To Implement Today

1. Ask about specific examples.

Judge people on what they did, not their self-assessed strengths. Gather insights by asking about the steps they took, their thought process, how they did the work, their learnings, and how they talk about the people or customers they worked with.

✅ THIS: Tell me about the most complex project that you managed.

❌ NOT: Can you do project management? Are you detail oriented?

By asking about real past experience, you reward doers over talkers.

Example follow up questions to dig in:

• Who did you work with? Tell me about their strengths and weaknesses.
• How did you keep people on track? What strategies and tools did you use?
• What were the goals and final results of the project?
• Did you hit any stumbling blocks? How did you overcome them?
• What lessons did you learn? Have you been able to apply them to any other projects?

2. Use skills-based questions or assessments.

Everyone wants to fairly and accurately evaluate someone’s skills but unless you know how to, you default to measuring someone’s confidence about said skills.

By getting these questions right, you’ll reward folks who are highly skilled but humble or self-deprecating and filter out folks who overestimate their abilities or talk eloquently but lack execution.

✅ THIS: Create and save a draft email in this demo account.

✅ THIS: Walk me through the basic steps you’d take to send an email.

❌ NOT: Do you know how to send emails? Have you sent emails before?

Predefine your assessment criteria and then rate the candidate’s competency. And, of course, focus on a skill that’s key to the role.

Example key actions to score:

• Pull a list of contacts
• Implement email design best practices
• Test email formatting in various email clients
• Strategize on a call-to-action
• Measure results

Examples of other skill-based activities:

• Whiteboard or code exercises for developers
• Create a financial model, pivot table, or other spreadsheet
• Write an email to an upset customer
• Make website recommendations to improve SEO or sales conversions
• Design a strategic plan for a real company issue

3. Go for superlative.

Asking about the most, least, greatest, proudest, hardest will get the best from a candidate. As the interviewer, you can be assured that you’re comparing one candidate’s best to another candidate’s best.

🙂 GOOD: Tell me about a project that you worked on.

😁 BETTER: Tell me about a complex project that you worked on.

🥳 BEST: Tell me about the most complex project you worked on.

If you ask a generic question about “a project” instead of “the most important project,” you won’t know if their underwhelming answer is because of their lackluster experience or your lackluster question.

What’s a question the most meaningful question you could ask? (See what I did there? 😉)

4. Keep questions consistent.

Ask the same interview questions at the same stages across all candidates for the most fair and insightful interview process.

When I first started interviewing and hiring, I thought asking a variety of interview questions was a strength. Foolish Young Kathryn could flip through her mental interview question database and ask according to her daily whim.

Unfortunately, this was a terrible idea!!

Asking different questions, while interesting to the interviewer, means that you’re comparing different data across candidates. You could unintentionally ask one candidate easier or harder questions. Keep it apples to apples to make it fair and unbiased.

Bonus: you only have to remember a handful of questions instead of hundreds like Foolish Young Kathryn!

5. Listen.

Give lots of time for a candidate to answer. Don’t jump in with the next question. Pause an extra moment to see if they have more to share.

What people share in the quiet moments can be really important.

Another strategy is to keep track of how much each person speaks. The candidate should be speaking the most (unless you’re answering their questions).

Listen deeply to what they say, how they say it, and what isn’t said.

Great Questions Lead To Great Talent

When you ask the right questions and listen well, you will easily identify top talent and win them over. The experience feels fair, their expertise and abilities shine, and you can move forward quickly and confidently.

The right interview questions are a great start to a long relationship with your company!

Hiring great people is essential to growing and scaling your startup. Interns are a key part of this strategy, especially in the early days. Most founders I speak to are looking for one (or many 😉) interns at any given time.

I love interns and keep in touch with many that I worked with. Lots of them have gone onto great things. Why? Students applying to business jobs in college are incredible!!

Interns are one of the best values in business. Get top talent at a fraction of the price in exchange for offering them coaching and experience.

(Note: I’m a huge believer in always paying your interns fairly. It’s the right thing to do, you’ll get a wider talent pool, and they’re more likely to stay on or refer other interns. It’s still a great value compared to what you’ll pay for a recent grad of the same caliber.)

To get started on finding your own powerhouse interns, here’s an overview of the process I’ve used to attract, vet, and retain the very best candidates.

7 Steps To Find (& Win) Outstanding Startup Interns

1. Job Description

First things first. Align internally on the projects and tasks for the role and turn it into a job description.

A Great Job Description Will:

• Showcase your company’s brand and personality - make a great first impression!
• Be positive but accurate about the work. Misaligned expectations = big headaches later.
• Highlight startup competitive advantages like interfacing with customers, doing meaningful work, exposure to a variety of projects, and working directly with the CEO
• Appeal to a wide range of candidates. Follow these tips to remove gender bias.

How To Promote:

• Post to college career sites, co-working sites, your social profiles, local channels.
• Share with your network especially previous interns, other employees, folks with college connections.
• Avoid the big name, mainstream career sites to start. Very noisy. Start with the targeted options first.

2. Resume Review

Once your job posting is out in the world, it’s resume time. I try to review daily in batches and follow up quickly with top candidates.

What To Assess:

• Leadership experience (clubs, sports, side hustles)
• Work experience
• Resume organization, clarity, and writing
• GPA
• GPA and job performance are correlated when you're in or just out of school. The more work experience you have, the less it matters.
• Take into account the average GPA for the school.

Look at all of these items holistically. If someone has a lower GPA but put themself through school and started a company, that’s pretty awesome. If they have a high GPA but no other activities or work experience, they may not have the practical work skills for a startup.

When on the fence, I usually give the candidate the benefit of the doubt and set up a video chat.

3. 15 Min Video Chat

It’s a quick intro on both sides. You can learn a lot in a short time.

What To Assess:

• Professionalism - on time, dressed appropriately
• Preparation - researched the company or team
• Social Skills - general politeness, will they be good in front of customers?
• Role Alignment - will they be happy in this role based on their goals?
• Positivity - any subtle complaining or blaming?
• Startup Compatibility - are they self-starting? can they handle change and ambiguity?

Example Questions:

• “How did you pick UniversityXYZ?”
• “What are you looking for in an internship?”
• “How did you prepare for our call?”
• “How did you hear about the role?”
• “Do you have any questions?”

4. Real Work Exercise

Great resume. Excellent video chat skills. Now it’s time to see — can they do the work?

This can be a coding exercise, a work sample, or — my favorite — a take-home activity that involves writing, thinking, and light research.

This step also gives the candidate a chance to understand what the day-to-day work is like.

Example Questions:

• Event XYZ is coming up. Write an announcement for LinkedIn and Twitter.
• Customer is upset because of XYZ. Draft an email reply.
• Research 3 locations for a team event with criteria ABC.
• Our ideal customer is ABC. Find 3 leads with contact information.

What To Assess:

• Writing Quality - clarity, grammar, consciseness
• Thought Process - thorough, logical, smart
• Conscientiousness - done correctly, on-time
• Can they do the work at hand?

(Note: Answers don’t need to be perfect! Especially for interns. Problem-solving skills, effort, and coachability are key. )

5. In-Person Interview

If they’ve made it to this stage, you’re getting close. Here’s where you drill in on specifics or concerns, meet others on the team, and continue to win them over!

What To Assess:

• Experience & Project Details
• Cross-Functional Fit - can they work well across the company?
• Core Values Alignment - do they embody your Core Values?

Example Questions:

• “What project are you most proud of? Why?”
• “What was the most challenging customer situation you faced?”
• “What was the most complex event you led? How did you stay organized and handle problems when they came up?”
• “Tell me about a time that you <did action that aligned with company Core Value>.”
• “What’s the hardest group project that you worked on? Why? How did you work through it personally and as a group?”

Address their questions throughout but especially at this stage. Understand their priorities or objections and speak to those. Always be closing!

6. The Offer

Speed is your friend. Big firms (or indecisive startups) move slowly. College students want to be done and get back to their other day job. Make it easy for them to choose you.

This can be as simple as a Google Doc with a company logo that you tweak for each new hire. (Convert to a PDF before sending.)

Information To Include:

• Job title
• Compensation (e.g. hourly rate)
• Hours per week limits or expectations
• Job responsibilities
• Start and end dates
• Other benefits and perks
• Why your company and this opportunity are awesome
• Why you want them
• A friendly welcome

Remember - this isn’t just a transactional document or contract. The tone and content of your offer letter will help close the deal!

7. An Internship They Love

Now that you’ve got them onboard, here’s how to keep them happy and make the most of the experience for you and them.

Top Strategies For Happy Interns:

• Pay them!
• Paid internships level the playing field so students of all economic situations can join you
• Great for recruiting 💪
• Some common ranges for startups in the Southeast
• $10-15 non-engineering
• $18-20 engineering
• Ask them to do work that matters.
• Share business tips, advice, and company insights.
• Provide opportunities to do or learn about their areas of interest.
• Be appreciative — say thanks and acknowledge their work within the company.
• See if they have referrals for future interns!

BONUS - Future Full-Time Hires!

Interns are a fantastic pipeline for full-time hires. Do you have an amazing intern and want to snag them after graduation? Make an offer as soon as you can. Lock it in before they start getting recruited or think about applying elsewhere.

Two Final Thoughts

1. Give yourself time to calibrate your talent compass.

It may take 10-20 candidates before you get a feel for what “good” looks like. Over time, the “A” players will stand out quickly.

2. Be kind and win people over at every stage.

At Pardot, we got referrals from candidates who didn’t get hired but they had such a positive experience in the interview process, they told their friends to apply. It was one of the best compliments.

The interview process is nerve-racking and time consuming for candidates. Being organized, thoughtful, and making candidates feel good, regardless of the outcome, is a powerful (and free!) flywheel for your company’s recruiting and growth engine!

What other strategies have you used to hire great interns? Do you have other steps or recommendations for the process?

Going From Early Stage To Unicorn

Last week, I shared Part 1: 4 Strategies Unicorn Founders Embrace. This week – surprise — we’re sharing Part 2 with more unicorn founder strategies.

These posts were inspired by an early stage founder with big goals who asked great questions:

Now that I’ve raised money and have passionate customers – what’s next? How do I build a unicorn, think like a unicorn, execute like a unicorn?

Here are 4 (more) common themes and strategies from unicorn founders to guide you and inspire you along your journey! 🦄

4 More Strategies That Unicorn Founders Embrace

1. Define your mission, pitch, and values.

Spend time crafting clear, concise:

• Mission statement
• One-line pitch
• Core values

Then talk about those things ALL. THE. TIME.

Why? These cornerstone elements will help:

• Attract candidates
• Hire faster
• Bring in new deals
• Close deals
• Drive performance
• Build a unique and powerful culture that people want to be a part of

Infinite Giving does an amazing job:

• Mission statement: leverage modern financial technology to grow the world’s giving
• One-line pitch: automated investment platform for non-profits
• Core values: Be kind and do excellent work.

Because they are simple, easy to remember, and communicated weekly by their awesome CEO, Karen Houghton, I can repeat them to anyone (aka future customers or hires) and I understand exactly what they do. This clarity helps throughout the sales funnel, hiring funnel, and company growth!  

David Cummings has long been a proponent of culture and core values with some great, specific blog posts if you want more.

2. Move fast.

One trend I’ve seen from unicorn founders – they have a bias for action and make decisions quickly. Speed is a key advantage especially against incumbents or other up-and-comers in the market.

3 Keys To Moving Fast:

1. Be responsive when asked for a decision.
2. Empower others to make decisions. (I mention my favorite delegation framework here.)
3. Have clear goals and core values (see Strategy #1) that serve as a decision-making guide.

In other words, avoid a CEO bottleneck.

A bonus of this approach is more time and energy for you to spend on hard-to-undo, strategic decisions.

3. Accelerate your rate of learning.

Kyle Porter, CEO of Salesloft, shared this advice at Salesloft in the Studio (43:00) and David Cummings’ also recounted it.

The concept is simple. Learn aggressively so you can grow faster than your startup is growing. Set up systems like peer groups, executive coaching, and daily business reading to turbo charge your personal growth. More suggestions here.

4.  Be confident.

Here’s the thing…

Every founder, no matter how successful, has something they’re insecure about. Unicorn founders are not exempt from imposter syndrome.

I’ve talked to wildly successful founders, who exude public confidence, and privately tell me things like:

• I got lucky.
• I don’t know what I’m doing.
• I have good people around me.
• When we hit <next milestone>, the wheels will fall off.
• I’m terrified of <normal CEO thing like public speaking>.
• This <other unicorn founder> is so much better than me at _____.

Why am I sharing this?

If you are feeling worried or insecure, that doesn’t mean you can’t do it.

It means you’re a perfectly normal unicorn founder!

Go to your place of resilience and strength:

• Rephrase “I don’t know” into “I can’t wait to learn.”
• Do it anyway.
• Pray.
• Fake it ‘til you make it.
• Reflect on your past successes.
• Think about your vision and your why.
• Call your #1 superfan for a pep talk.

And then keep going.

Amazing things are ahead! 🚀🦄

What other strategies do unicorn founders embrace? What have you seen or experienced with unicorn founders that helps them build?

“How do I go from early stage to unicorn?”

I recently met with a fantastic founder who raised her hand when I shared the goal of 10 female unicorns in 10 years.

She’s picked a big market and she’s secured funding. What’s next, she asked? What have you seen in unicorn companies and founders?

[Kathryn’s note: What a great question. Clearly thinking like a unicorn founder already!]

What are the strategies or characteristics of companies that cross over that $1 billion valuation mark?

Specifically – what’s within a founder’s control that they can start doing today?

Here’s the first 4 strategies that unicorn founders use to take them from $1 to $1 billion. Check in next week for Part 2!

4 Strategies That Unicorn Founders Embrace

1. Pick a big market.

I’m a broken record on this one. The first step to being a unicorn is being in a big market! No matter how amazing your leadership or product, you can’t build a billion dollar company in a small market. It’s way easier (and more probable) to grab 1% of a $100B market than grab 100% of a billion dollar market.

Think your market isn’t big enough? Adjust your strategy or pick a new idea.

You can also build a great small to mid-size business. Be clear on your personal goals to decide what’s right for you.

2. Embrace 10x thinking.

In the early days, the question is: how do we get 1 more customer?

When you’ve found product market fit (in your HUGE market), it’s easy to continue that pattern: how do we get a few more customers?

In a unicorn mindset, you ask, how do we get 10x more customers?!?

It’s straight out of the Google playbook. They’ve built a pretty nice business 😉

Try it at your next strategy or planning session. Take a problem or goal and brainstorm what 10x looks like. How do you get there? What big ideas does it trigger?

3. Stay focused.

Once you find product market fit, optimize for your ideal customer.

Design your marketing programs, sales process, and product roadmap for this ideal customer. Do not get distracted by shiny objects!!

Examples of shiny objects:

• enterprise deals that aren’t a good fit
• one-off product features
• marketing to fringe user segments
• a new product line or platform before you’re ready

Pardot was fantastic at this focus. We knew our sweet spot was SMBs. We didn’t chase enterprise deals or crazy technical requirements (even though our competitors did). We followed the 80/20 rule with product development and only added a feature if 80% of our customers could use it.

As a result, we had strong retention, a repeatable sales process, and scaled faster in the long run.

4. Settle in.

Building a unicorn is the fastest marathon of your life. On average, it takes 10 years for a startup to reach unicorn status. It will feel fast and slow all at once!

Be prepared for the long haul. Everything is urgent and crazy – and it will be for 10 years! Figure out ways to take care of your physical and mental health along the way.

But wait…

…there’s more! Tune in next week for 4 more strategies for building unicorns. 🦄

I had the honor of grabbing coffee with the brilliant and fun Susan Cohen, business professor at University of Georgia and leading expert on startup accelerators.

If you haven’t had the privilege of working with her as a mentor, following her on Twitter, or taking her entrepreneurship class…NEVER FEAR!

We crammed decades of research and experience into a 60 minute chat and now I’ve distilled that into 6 practical, actionable gems to maximize your accelerator experience.

Thank you, Professor Cohen, for generously sharing your knowledge with startup founders and leaders.

1. Accelerators work!

A good program can:

• Accelerate customer traction
• Shorten time to raise
• Increase the amount raised
• Shorten time to exit

Accelerators also increase the influx of investment into startups in the region. Not just to the startups at the accelerator but to other startups in the market as well. So even if you don’t get into that local accelerator, know that it may still be helping you long term!

2. Not all accelerators are created equal.

There are good accelerators and not-so-good ones. What should you consider when evaluating an accelerator?

• Deal Terms
• Most accelerators take a % of ownership in exchange for seed capital.
• Are the terms similar to other accelerators?
• Is the value of the accelerator worth the dilution?
• Mentorship
• Who are the mentors and how can they help your business?
• Resist the sway of big names. The best athletes are not necessarily the best coaches.  
• Some of the best mentors are founders a bit ahead of you.
• Do the mentors have experience in your industry and company size? A great tennis coach won’t help you play basketball.
• Multiple mentors per entrepreneur is better than a single dedicated mentor. A variety of opinions, backgrounds, and personalities is key.
• Managing Director
• What’s their background?
• Are they a previous founder? Investor?
• How’s their network? Will it help your business?
• Track Record
• Have companies similar to yours graduated from the program? How have they fared?
• Talk to alums of the program and ask about their experience.

3. Accelerator fit matters. A lot.

Pick the right accelerator based on your industry, target customer, geography, business model, and personality.

Geography matters - a good accelerator will exponentially grow your network. Where do you want your future network?

If you are a hardware company at a mostly SaaS accelerator, the learnings, mentors, and peer relationships may not be as helpful as a hardware accelerator.

If you sell to government and everyone else in your group sells to SMB, the customer traction process may be wildly different. Or maybe you’re pre-product and everyone else has a product already.

If you sell to the accelerators’ alumni base — other startups, for example — that’s a home run!

Being in the wrong accelerator even if you can “get in” has potentially negative downstream effects:

• Waste of time
• Discouraging
• Negative investor perception

If you go through top tier accelerator and don’t get funded, investors assume something was wrong even you’re a great founder with a great business.

4. Attend all sessions. Meet all people.

What accelerator style performs better?

• (A) Customized sessions and mentors for each company
• (B) Standardized tracks regardless of product, market, or founder experience

Surprise! Even the most innovative, creative founders do best on (B) – the standardized track.

Why?

• We’re not as smart and special as we think. (Except for you. YOU are a unique snowflake. I’m talking about the others 😉)
• If we’re already knowledgeable about a topic, our default is to opt out:
• “I know how to play tennis, I don’t need a tennis lesson.”
• But if we have previous experience, we’re better able to learn MORE:
• “Because I already know the basics of tennis, I can fine tune my game. I’ll get more out of a tennis lesson than someone who doesn’t know tennis at all.”
• Varying levels of knowledge in each session helps entrepreneurs learn from each other. The former-CPA founder learns from the former-CMO founder and vice versa.

5. Leverage the peer group.

One of the best parts of accelerators is the founder/CEO peer group. Starting a company is lonely and hard. Having others that understand can help you weather the roller coaster.

Peers also increase the speed of learning and execution. You push yourself harder when others around you are pushing too.

Achievement inspires achievement: “If they can do it, so can I!”

Peer-to-peer learning tends to be more tactical. It’s a quick question via Slack. One question to a peer could save you a whole day of research or testing.

Professor Cohen puts it best:

You learn strategy from your mentors. You learn execution from your peers.

6. Make the most of mentors.

Step 1: Listen for different ideas

Mentors may suggest advice that conflicts with your own ideas.

Most entrepreneurs (ahem, most people) hear advice that jives with their own ideas louder than advice that conflicts with their ideas. Resist this temptation and listen for advice that is different.

The goal of advising sessions is to deepen your understanding, not to confirm what you already know.

Step 2: Listen for trends across advisors

Keep track of what different mentors say to see where they agree and where they don’t. If you keep hearing similar advice over and over, the general advice is probably right.

For example, if you keep hearing suggestions about your business model, even if the details differ, you probably need to re-examine your business model.

Bonus! Ask for ideas about alternative business models in your next mentor meeting.

Step 3: Test it!

Advice is not take it or leave it. When in doubt, test it! Design a quick test to gather data and assess the results.

Need help? Work with a mentor to craft a lightweight test.

Want More Accelerator and Startup Research?

Do you love these learnings from Professor Cohen? (I do!!!) For more awesome research and insights, check her out on LinkedIn, Twitter, or read the research:

• The Role of Accelerator Designs in Mitigating Bounded Rationality in New Ventures
• What Do Accelerators Do? Insights from Incubators and Angels
• Do accelerators work?

Extra Credit — take her evening MBA class at UGA’s Terry School of Business in Lenox!

She’s a startup mentor, angel investor, and huge asset to entrepreneurs everywhere. 🙏🙏🙏

I recently warned against “set it and forget it” productivity strategies. Your calendar, inbox, and workflows need regular review to keep them manageable.  

Gardens need tending, closets need clean outs, and work systems need audits!

Use this checklist of topics and questions to periodically review your systems and time allocation so you can stay efficient, energized, and focused.

I’d recommend a productivity audit 1x/quarter or whenever you’re falling behind on key priorities and need a reset.

Productivity is not getting lots of things done. It’s getting the important things done!

1. Priorities Audit

Am I spending time on the right stuff?

It’s easy to get stuck reacting to fire drills, one-off requests, new ideas, and other startup busyness.

The first step of a productivity audit is reviewing the big picture.

Priorities Questions

• What are the most important things personally and professionally?
• What specific goals did you lay out for yourself or the company?
• How are you tracking towards those priorities and goals?
• How are you spending your time now? (Check your cal or track your time for a day.)
• Do any of the goals or priorities need to be recalibrated based on a change in circumstances? (e.g. you added 10x more customers than expected and it’s all hands on deck – a good reason to recalibrate!)
• What needs to be canceled or changed to make more time for the priorities?

#protip

Eisenhower Matrix is a great tool to organize work by importance and urgency.

2. Meeting Audit

Are your regular meetings still productive and necessary?

Meeting creep is a thing. One more meeting here and there isn’t a big deal until you’re only free from 8pm to midnight.

Projects wind down, strategic priorities change, roadblocks resolve, and new hires need less hand holding. Review your meetings to make sure they’re still important and helpful.

Meeting Questions

Could any meetings be…

• Moved to every other week or monthly?
• An email instead?
• A Slack channel or thread?
• Combined with another meeting?
• Shortened by 15 min or cut in half?
• Improved with a new format?
• Canceled?
• Handed off to someone else?
• Declined because you don’t need to be there?

#protip

Block one day per week with no meetings. We had company-wide “Freestyle Friday” at Pardot and “Yoursday Thursday” at Rigor. Everyone loved the deep work and productivity.

3. Direct Report Audit

How are your direct reports doing? Does the reporting structure make sense?

When startups grow quickly, the org structure changes constantly. New hires join, senior leadership is brought in, departments and roles are added.

Here’s a few examples of things that happen when you grow fast:

• too many direct reports with one person
• an early “utility player” hire that could use an experienced manager
• the junior person reporting to the CEO because “they always have”  

Thinking about time and energy spent on your direct reports is helpful to identify problem areas and possible solutions.

Direct Report Questions

• Are folks happy? Any attrition risks?
• What new challenges or opportunities might be interesting for someone?
• Is anyone ready to be promoted?
• Could someone be a “team lead” to help coach and mentor new hires?
• Any difficult conversations to have about performance or reporting structure?
• Any new hires to make?
• Is your number of direct reports manageable?
• Are you spending an appropriate amount of time on people management?
• Is external training, coaching, or mentoring needed?  
• What can a direct report own to free up your time and also help them grow?

#protip

5-7 people is a reasonable number of direct reports. It could scale up to 10 when you’re growing quickly and building out teams. It could be 2-4 if you have other responsibilities.

4. Task Audit

What daily or weekly tasks are most time consuming? Are they a good use of your time?

The wise Bob Lewis speaks about the “best and highest use of time.”

Yes, the CEO can answer a support ticket. But is that the best use of her time? While she’s answering the support ticket, who is cultivating strategic partnerships, recruiting executive talent, and communicating company vision?!?

Only the CEO can do those. So while she can answer support tickets, she should focus on work that is the best and highest use of her time.

This applies to all roles! Delegate, automate, or discontinue tasks that don’t align with the best use of your time.

Task Questions

• What tasks can be streamlined by tools like Calendly, Zapier, or TextExpander?
• What items would be easier with CRM, marketing automation, or support platforms?
• Is it time for a virtual assistant, grocery delivery, MyPanda, or meal service?
• Can you hire an intern or contractor to own certain projects?
• What tasks or projects could be handled by someone else on your team?
• What tasks are no longer important and can be dropped?
• What tasks keep falling through the cracks? Why?
• Can a task be combined with something else, like scheduling a regular call during your commute?
• If you didn’t do it, what would happen? Would someone else do it? Would it not matter? Will it get handled later?
• Can you make it easier or more fun by working as a group or gamifying?

#protip

Don’t feel guilty about delegating! What’s “boring” to you may be an interesting, challenging growth opportunity for someone else. Explain your expectations about the work, why it matters, and express gratitude. Here’s my favorite framework for delegation decisions.  

5. Friction & Fatigue Audit

What feels harder than it should? What is wearing you down?

This is a catch-all category to identify any other frustrations or pain points in your workflow, schedule, or overall energy.

Friction & Fatigue Questions

• Do you feel fulfilled, energized, and interested on a daily basis?
• Is there something you’re spending way too much time on?
• Do you dread XYZ each week?
• Is there anyone that you don’t want to talk to anymore?
• Are you taking care of your basic health needs like sleep, social connection, physical activity, and nutrition?

#protip

Productivity isn’t about being a work robot! Listen to your feelings or gut reactions to guide you towards improvements.

What other items do you look at when assessing your productivity? What should be included in a productivity audit?

Startups (and life) can be busy and hectic. Having good systems is key to managing the chaos and staying on top of tasks and projects.

I’ve already shared my 3 favorite strategies for staying organized and efficient. Today, we’re going to cover some common productivity misconceptions.

These myths hold people back from their best, most-productive selves. They induce people to focus on the wrong things, judge themselves unnecessarily, and get discouraged.

Let’s deconstruct these 6 productivity myths so we can get back on track with simplicity, consistency, and efficiency.

6 Productivity Myths To Watch Out For

Productivity Myth #1

I bought this new tool/planner/colored pen/magic rock and now I’ll be able to get organized!

In my experience, more tools do not equal more organization. It just means more to keep track of, more places to update, and more complexity. When in doubt, simplify.

Productivity Myth #2

One item slipped through the cracks, therefore this system doesn’t work.

It takes a bit to get the hang of any new system and customize it to your needs. Give yourself time and wiggle room as you get started.

Productivity Myth #3

When I have the right system, everything will be perfect.

No organization system or tool is perfect. Even when you have things dialed in, these systems depend on humans. And sometimes humans make mistakes - gasp!

Don’t get distracted by outliers or one-time exceptions. If these “exceptions” happen regularly, then they are no longer exceptions and you should plan for them in your normal workflow. Otherwise, figure out the one-time game plan or chalk it up to a fringe case and get back to work.

Productivity Myth #4

Set it and forget it.

I like to run as many things as possible on autopilot. Especially if they are repetitive or not a good use of time. But life and startups change pretty fast. Always revisit your systems to see if they are still serving you!

Plan a quarterly audit. Or pay attention to your stress levels, what tasks are most time consuming, or when you start dropping balls.

I regularly review my systems, schedule, workflows, inbox, and to-do items to see if something needs to be dropped, changed, or added.

Productivity Myth #5

Hit Inbox Zero every day.

Inbox Zero is beautiful and calming. It’s heralded by many as the pinnacle of productivity.

I get there a few times per week but I don’t make it a daily goal. As long as I have confirmed that all time-sensitive items are taken care of, I’m okay letting some things hang out until the next day.

I find that sleep and letting my brain reset are more important to my overall productivity than daily Inbox Zero. I rule my inbox. It doesn’t rule me!

Productivity Myth #6

Sleep less to get more done.

Sleep is really important. It makes you smarter, able to work more quickly, and stay calm and happy. All of those things are fantastic for productivity.

The next time you want to stay up late to get more done, get a good night’s sleep instead. You’ll be able to tackle that work in the morning and get it done better, in less time, and feel happier.

2 Things That Work!

If you’re working to be more organized and productive, don’t let these myths derail you. Productivity strategies are never one size fits all, but I’ve seen two recurring themes when people have systems that work.

1. Simplicity

• Use as few tools as possible.
• Stay as close to the “source” of the work or communication as possible. If you work mostly in email, stay in email. If you use Slack all the time, make that your main tool for organization.
• Adding extra steps or transferring to-dos from one system to another leads to mistakes and process fatigue.

2. Consistency

• An organization system only works if you follow it!
• Pick something that makes sense for your personality, role, and lifestyle.
• A decent system executed consistently is better than a “perfect” system implemented every few weeks. Do small tests and tweaks, not overhauls.

What are some productivity misconceptions that you’ve come across? What productivity tips have hurt your productivity?

A Passion For Productivity

I’m into efficient systems. I’ve led company training sessions on emails, calendar management, time saving tricks, follow ups, agendas, project planning, and more. My closet has been color coordinated since age 9. One of my favorite gifts is my “Get Shit Done” mug.

I love trying out new tips or strategies and iterating my approach. After a decade in tech startups and many decades as a type A nerd, here are the top 3 strategies I use to stay productive and organized.

3 Simple Strategies To Stay Organized

1. Inbox as a To-do List

Shout out to the original efficiency guru TJ Gephart who taught me this one – Inbox as a To-do List for the win!

How It Works

• If it’s in your inbox, you need to take action on it.
• Once you’ve taken action, archive the email.
• If you haven’t done the thing, keep it in your inbox.
• Ta-da! Your inbox has become your to-do list.

Why I Love It

• One source of truth. I don’t check my to-do app, planner, calendar, email, notebook, spreadsheet, and project tool to find out what’s going on. I go to one place for all my action items. And I go to that place all the time anyway!
• Clear inbox. Full brain. Can’t lose (track of it). Once you archive an email, you can find it if you need it. But it’s not taking up physical or mental space in your inbox. Brain power is preserved for things that need it.

In Action

Only 11 emails. 1 is going to be archived. 10 items left that need to be reviewed, followed up on, or serve as reminders.

ProTips

• Want to track a non-email item? Send yourself an email.
• Send follow up emails with next steps. It’s helpful to meeting attendees and now you’ve got the action items in your inbox.  
• Use calendar reminder emails for meeting follow up. I get email alerts for any meetings on my calendar. That email stays in my inbox until I’ve sent a thank you, made the intro, or sent the article from that meeting.
• Snooze. If I don’t know how to respond to something or am not yet ready to make a decision, I kick the can a few hours or days with Snooze. Sometimes I’ll have an email-as-a-reminder about a longer term project. If I can’t get to it this week or month, Snooze that thing for 30 days. It’s not taking up headspace but you know you won’t forget!
• If you don’t know what Snooze or Archive is, switch to Gmail!

2. Calendar Blocks

How It Works

• I block time on my calendar for projects or any non-meeting work that takes >15 min.

Why I Love It

• Visual understanding and accountability for my to-do list!
• Realistically plan what can get done and when
• Helps you make time for important “deep work” things like writing or presentations

In Action

Example calendar that’s mix of “real” meetings and time blocks for priority projects.

ProTips

• Plan for 2x more time than you think on any given project or task. Humans are beautifully optimistic. We always think it’s going to be easy and we’ll go fast. This is true .0001% of the time. Give yourself more buffer than you think.
• Use your calendar to set expectations and manage workload. Because you see your availability on your calendar, you can easily clarify timelines and priorities:
• “I am committed to other projects this week but should be able to get to this next week.”
• “I was planning on completing ABC today. Should I swap that to prioritize XYZ instead?”

3. Sticky Notes

Going old school, non-tech for the last one. Stay with me!

How It Works

• I keep high priority items on a sticky note next to my laptop.
• When I get sucked into the vortex of Slack/email/internet memes, the paper note outside the digital black hole helps me refocus on that day’s must-do items.
• “Must-dos” can range from 5 - 7 small items or 1 big one.

How It Works (Personal Variation)

• For my personal life, I have a 3-item to-do list.
• ONLY 3 ITEMS ALLOWED!
• Complete an item? Yay! I get to add a new item.
• An urgent item came up? That’s cool. I’ll take something else off for now.  
• If I see 12 things, I get overwhelmed and do nothing. With 3 items, I pick one and get started.

In Action

Gee. I wonder what’s important today?

ProTips

• Splurge and get the Post-It brand sticky notes. Knock off brands don’t stick well. (I have some off brand ones you’re welcome to try if you don’t believe me...)
• If you’re worried about not remembering your “other” to-dos, feel free to keep a master list.  I like the fluid, organic process of identifying my personal to-dos as they come up, but it can relieve stress to have a place to jot items down.  

BONUS: Tech Recs

Other Tools I Use

• Google Drive: Docs, Spreadsheets, Slides, Forms
• Google Keep: Lightweight note-keeping - similar to Evernote. I use it for collaborative lists with my family (shopping, packing, house projects) or saving random thoughts.

Tools My Productive Friends Use

I don’t personally use these but trusted sources speak highly of them.

• Todoist - task tracking
• Google Tasks - within Gmail interface, seamless syncing across GSuite
• Superhuman - clean, fast email interface
• Things - task tracking app
• Getting Things Done - a classic how-to-stay-organized book

How Do You Stay Organized?

Organization and productivity is never one size fits all. The right system varies based on your personality, job, company culture, tech stack, daily workflow, and more.

What tools or systems work for you?