5 Strategies For Annual Planning Success Despite Startup Chaos
You make annual plans. You set out metrics. Then…startup life happens. How do you follow through on your annual plans and goals despite (completely normal) startup chaos?
Read More
You make annual plans. You set out metrics. Then…startup life happens. How do you follow through on your annual plans and goals despite (completely normal) startup chaos?
Read MoreEveryone has a plan until they get punched in the mouth.
- Mike Tyson, startup guru
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Okay, so he’s not a startup guru (that I know of) but this quote always reminds me of startup life.
Just one big punch in the mouth!
JK. JK. JK.
You make annual plans.
You set out metrics.
Then…the app crashes, your top customer wants to quit, fundraising takes longer than expected, and you can’t find engineers.
How do you follow through on your annual plans and goals despite normal startup chaos?
Here are 5 steps to ensure you achieve your annual goals!
You’ll be as motivated and focused in December as you are in January.
There’s 100 different options for annual planning.
(We shared 5 of our favorites last week.)
Choose a goal setting framework or philosophy that feels easy and effective for YOU.
Which framework are you most drawn to?
The best framework is one that resonates with your style and values.
Where will you see and feel your annual goals every day?
Ideally, you’re “touching” them by writing them, discussing them, updating metrics, or something that keeps them alive.
Static goals quickly become part of the scenery.
Top-of-Mind Ideas:
At Rigor, we added a mid-quarter check-in for our strategic goals.
Why?
We would be preparing our end-of-quarter recaps and realize something totally fell off our radar. (It happened to everyone at one time or another!)
Having a preset meeting to discuss progress on long term goals is a great way to maintain focus.
Do you know accountability isn’t your strong suit? Do you get busy and have trouble following through?
Behold…
Potential Accountability Resources:
Twelve months can be a lifetime at a startup. What made sense in January may not be a priority in December.
Goals serve you.
Don’t mindlessly strive for goals that aren’t the best and highest use of your time because you “wrote it on the paper” in January.
(I am sooooo guilty of this. MUST…FOLLOW…THROUGH…)
If you haven’t made progress on your annual goals, why not?
Be honest with yourself and course correct accordingly.
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What strategies help you and your company stick with your annual goals? Any tips or stories to share?
As you head into company annual planning and 2023 goal setting, here are 5 awesome tools to help facilitate the process.
Read More2023 is just around the corner!
(Kathryn frantically orders gifts on Amazon…)
As you head into company annual planning and 2023 goal setting, here are 5 awesome tools to help facilitate the process.
Pick one to anchor around or incorporate aspects of all five. Being thoughtful now will pay dividends as you attack the new year!
A David Cummings classic. It works for large companies, individuals, teams, projects, personal, work, and everything in between.
Here’s the downloadable template.
Take a goal from vague pipe dream to Specific, Measurable, Achievable, Relevant, and Time-bound.
Whatever planning or goal setting framework you use, SMART goals always apply!
When we implemented the “SMART” principles to our quarterly planning process at Rigor, it changed the conversation. We stopped debating whether a goal was achieved and started talking about improvements, next iterations, or digging in on “why” something worked or didn’t.
The Objectives and Key Results framework, initially created by Andrew Grove at Intel and popularized when John Doerr brought it to Google (and wrote a book about it).
It’s a great option for product or non-revenue projects and can be used at companies large and small.
I’ve said it before and I’ll say it again. Atomic Habits is amazing.
James Clear wrote one of the most popular (4.8 out of 5 stars) and transformational books on how to change your life through habits.
You are what you do. You do what’s easy. How do you make it easy to achieve your goals? Build it into your daily workflow so it becomes automatic. Systems over goals.
Well-known business operating methodology that incorporates vision, data, goal setting, meeting cadences, and more.
If the Simple Strategic Plan is the Cliff Notes, Traction (aka Entrepreneur Operating System — well branded, Mr. Wickman) is the end-to-end handbook.
Read the book (not to be confused with THIS Traction book - also highly recommended) and see which aspects work for your company.
…is the one that works for you!
Maybe you hate plans but love habits. Or you need something you can complete in less than an hour. Or you need something that can support a larger team.
Identify what what resonates with you at this stage.
Your process should feel meaningful and easy to maintain.
Speaking of maintaining…how do you stay on top of annual goals amidst startup and life chaos??!! We’ll talk next week about simple ways to build accountability and goal tracking into every day life.
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What tools do you use for annual planning? What goal and planning frameworks work well at your company?
Creativity, thoughtfulness, and personal touches make the most memorable gifts. Here are 10 ideas for employee gifts and celebrations (including low cost and remote friendly options) this holiday season!
Read MoreHow are you thanking your employees this year??
You got the customer gifts handled (whew) and you realized…oh crap, what about my team!?!?
We got you.
Distributed team?
Got you.
Working on a tight budget?
Still got you.
As we learned from customer gifts, it’s not the money that matters. Creativity, thoughtfulness, and personal touches make the most memorable gifts.
For the busy startup leaders, here’s 10 ideas for employee gifts and celebrations (including low cost and remote friendly options) this holiday season!
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What has been your favorite gift given or received? Other fun or creative suggestions?
In case you missed the memo, it’s customer gift season! We shared customer gift timelines. We shared specific gift suggestions. Today we cover real life customer gifts and the surprising lessons learned!
Read MoreIn case you missed the memo (here and here), it’s customer gift season!
We shared customer gift timelines.
We shared specific gift suggestions.
Today we cover real life customer gifts and the surprising lessons learned!
In the early years of Pardot, we gave $100 Amazon gift cards (physical ones) with handwritten thank you notes to our top users. Pretty nice gift, right?
When Pardot was acquired by Exact Target, we suddenly had Big Company Marketing Energy.
Behold…the custom, branded cookie basket.
Cookies in the shape of an email icon, logos and company colors on everything, hot cocoa and a mug to complete the cozy vibe.
Cute but affordable. $40 per basket (with bulk discount).
Our customers freaking LOVED THEM.
I got more enthusiastic thank yous from a $40 cookie basket than from thousands of dollars of gift cards.
LESSON LEARNED:
Thoughtful, branded, and creative gifts beat out expensive and generic ones.
The highest value swag of all time, hands down, were ceramic Rigor coffee mugs for $10 each.
Why so popular?
(DISCLAIMER: Not all engineers love coffee and swear words, okay??)
The mugs were simple, fun, a little bit edgy, and a perfect fit for our techie customers.
The idea was inspired by a coffee mug from the internet with the same phrase.
We added a logo and…
Voila! Customer gift magic!
LESSON LEARNED:
Find a great item that fits the personality and interests of your typical user. Like Lesson #1, creativity outperforms dollars spent.
It’s the gift I still talk about.
Strangers say, “The most incredible swag I ever got was…”
I finish their sentence. We’re always talking about the same gift.
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In December 2020, Rippling sent a box of four caramels to its customers.
Handmade caramels.
From a goat farm.
Owned by the sister of the Rippling CEO.
In the most beautiful packaging.
With a note from Parker Conrad about working from his sister’s Vermont goat farm during the pandemic.
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Do you need to have a sister who owns a goat farm to give a great gift?
Yes.
But if you don’t have a sister or a goat farm, is there a person or business in your life with a unique product?
What about a customer who has a gift-worthy item? Or a local company with a quirky brand?
Tell the why behind the gift and explain the personal connection. The present goes from mundane to goat-farm-magical with a heartfelt story.
LESSON LEARNED:
A well-executed personal connection or story makes a deeply memorable gift.
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What has been the most popular customer gift you’ve given or received? Any fun or noteworthy lessons learned?
It’s customer holiday gift season! What gifts should you give your clients? Here’s a list of 7 ideas and vendors with various price points, lead time, customization, and fanciness.
Read MoreIt’s customer holiday gift season!
We urgently, I mean, helpfully reminded you last week with a timeline, how-to suggestions, and brainstorming questions!
This week, we cut right to the chase.
What gifts should you give your clients?
Here’s a list of 7 ideas and vendors with various price points, lead time, customization, and fanciness.
All of these I’ve used, received, or had highly recommended from other founders.
Let’s gift to it!
Why We Love It:
Swag Up handles manufacturing, packing, shipping, and storing inventory. One-stop shop.
But I love storing and sorting through old swag…said no one ever!
Why We Love It:
Atlanta-based, woman-owned, and THEY KNOW WINE. Every wine recommendation I’ve had from Starbright has been perfect.
Why We Love It:
Woman-owned and “they are a DREAM to work with!” from a founder who used the service.
Great value alignment for companies with sustainability or do-good missions. (Um, which is hopefully all of us…)
Why We Love It:
Customer service and experience is incredible. On par with Zappos or Stitch Fix.
Robust product reviews help you decide on items. I’ve been happy with 4.5 stars or higher.
Why We Love It:
Great for teams. Send to the executive sponsor who will share with everyone in the office.
Can be sent quickly with minimal lead time. Good for birthdays, thank yous, and other celebratory items too.
Why We Love It:
Atlanta-based company that can do branded orders. Every day item that’s not your typical pen or tech t-shirt.
I have a 4 pack at home and would use at least 100 more.
Why We Love It:
High touch and custom. It’s a total flex if you know a customer well enough to send them something unique and personal.
Bonus: use in the sales process or for employee recognition too!
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Have you received or given a customer gift that was amazing? Other great customer gift brands or vendors to share?
We try not to be alarmist here on the O’Daily. Startup life has enough fire drills without adding to it. But here’s the reality. If you haven’t started planning holiday gifts for customers, you’re behind.
Read MoreWe try not to be alarmist here on the O’Daily. Startup life has enough fire drills without adding to it.
But here’s the reality.
If you haven’t started planning holiday gifts for customers, you’re behind.
But it’s the first week in November??? How could I be behind???
Yep, it snuck up on me too. It always does.
What I like to do is make an abbreviated plan for this year and then implement the “ideal” plan next year when I’ll have more time and be better prepared.
HAHAHAHAHAHAHA.
I really always think that though.
Luckily, it’s not too late to get a great customer gift plan in place!
Today, we’ll cover timelines, questions to consider, and how-tos of customer gift giving.
Next week, we’ll share suggestions on the type of gifts to give with specific recommendations and unexpected lessons learned from real customer gifts.
Let’s get to it. These gifts aren’t going to plan themselves!
Let’s work backwards.
You want gifts to arrive before everyone is out for holiday break. Out of town, out of the office, out of touch. You don’t want your $50 cookie box getting moldy during the 2 week ghost town between Christmas and New Year’s.
Some items take 5-10 days to arrive. Especially for the standard (read: most affordable), non-rush shipping option.
If you’re delivering to an office, there can also be a lag between mailroom arrival and when it gets into the hands of your customer.
Getting branded swag made takes time. So does putting together gift boxes, signing cards, coordinating a team photo, or whatever other prep items you do.
If you’re mailing a physical item, you’ll also need to confirm addresses which is extra fun in this work-from-anywhere world. 😁
Note: Businesses (including yours!) may be closed for 2-3 days over Thanksgiving.
Things to do next week: gift ideation, research, rough draft customer list, budget, get quotes (total cost + timeline), get final approval, place order.
No big deal though. Just another Tuesday in the fast paced world of startups! 😉
Take a few moments to identify the purpose of your holiday gift. It will help clarify your target audience, budget, and gift item.
Which users or customers should receive a gift? This can get complicated…
#PROTIP
Once you have a “who” plan, circulate a tentative spreadsheet of gift recipients. Other teammates, especially in sales or leadership, may have specific customers to add. Do it upfront to prevent leaving off someone important or not having enough gift supplies!
What’s your budget for this project?
#PROTIP
Order a few extra of everything. Typos, water spills, last minute additions, package malfunctions, internal requests – wiggle room comes in handy.
What kind of gift should it be?
#PROTIP
DIY is less expensive but takes (significantly) more time. There’s no right or wrong but be aware and intentional about the tradeoffs.
Where should this project live? Who handles the execution?
It’s 100% dependent on your company size and structure.
Corporate gifting is a $258 billion market for a reason.
(^^I have done all of these before. 🤪)
#PROTIP
We’ll have specific gift suggestions next week including some surprising learnings on what customers love. Spoiler Alert: it’s NOT the most expensive gift we sent.
Holiday gifts are a great way to stay in touch with customers and spread goodwill.
Start planning now so you can be thoughtful, thorough, and creative!
Other advice for customer holiday gifts? Any gifts or strategies that worked well?
Gratitude is important to cultivate in our lives and companies. It fosters happiness, clarity, abundance, and resilience. Like attracts like so when you are appreciative and positive, more good things come your way.
Read MoreGratitude is important to cultivate in our lives and companies. It fosters happiness, clarity, abundance, and resilience.
Like attracts like so when you are appreciative and positive, more good things come your way.
(Or you see the good things already there?!?)
At a startup, each stage is special and hard.
It's easy to focus on what's wrong or look ahead to what's next.
Only to realize afterwards how much fun it was at the previous stage!
(Also true for parenting, sports, learning new things, life in general...)
At startups, a genuine “thank you” can earn more goodwill than all the free snacks or company perks combined.
Gratitude can also be a source of strength through the low lows (that inevitably come with the high highs) of entrepreneurship.
Even on the hardest day, can you be grateful that you control your own destiny, don't work your old corporate job, or are working to make the world better?
You know you should. But how do you ACTUALLY capture more gratitude and appreciation in the moment?
It's a work in progress, but something that's worked well for me is a daily gratitude habit.
I make a list of 10-20 things that I'm grateful for every day.
I started doing it after taking The Science of Happiness, an amazing online course from Laurie Santos, professor at Yale.
Research shows exercise, sleep, gratitude, and social connection are more important for happiness than money, fame, or promotions.
Even though we think — and act like — it's the opposite…
Some items on my daily list are heartfelt and big. Some are silly and small. Some are things only appreciated when they're missing (health, air conditioning, a good night's sleep!!) so I try to recognize them proactively.
But that's the point, isn't it?
Once I get started, I realize I could go on and on. Husband, parents, neighbors, friends, housing, healthy food, bike paths, comfy shoes, hilarious squirrels, libraries, puzzles, modern medicine, eating outside, paying customers, smart engineers, a mentor to learn from, talented interns, a well-designed product, financial stability, a cup of coffee…to infinity.
What are you grateful for this week, this moment, this year, this life?
Personality assessments are amazing tools for early stage companies. Whether you’re a team of 5, 50, or 500, understanding who people are, how they work, and what motivates them is invaluable!
Read MorePersonality assessments are amazing tools for early stage companies.
Whether you’re a team of 5, 50, or 500, understanding who people are, how they work, and what motivates them is invaluable!
But not all personality assessments are created equal.
Below are my top 2 favorite personality assessments, pros and cons of each, plus a list of other assessment options.
Let the culture, clarity, and collaboration begin!
P.S. Clay Kirkland is the facilitator I’ve used for 10+ years and he is EXCELLENT!
What else is out there? Here are some others that I’ve done or heard recommended.
We’ll cover tips and tricks for how to make the process of company-wide assessments work well. Helpful, not (too) cheesy, with strong internal adoption!
Have you used personality assessments with your team? How did it go? Any tips or favorites to share?
I recently did a presentation on “Understanding Venture Capital” for this year’s Main Street Entrepreneurship Seed Fund cohort out of Georgia State University. I shared #protips on fundraising — lesser known tips and strategies for success when you’re going out to meet VCs and raise money. Here are 3 keys to fundraising that every entrepreneur should know!
Read MoreI recently did a presentation on “Understanding Venture Capital” for this year’s Main Street Entrepreneurship Seed Fund cohort out of Georgia State University.
I shared #protips on fundraising — lesser known tips and strategies for success when you’re going out to meet VCs and raise money.
Here are 3 keys to fundraising that every entrepreneur should know!
Investors love intros from other entrepreneurs, especially those in their portfolio.
🤔 Why?
Service providers— lawyers, accountants or consultants—may have a great intro, but they also have a clear economic interest in seeing a company raise money.
An entrepreneur intro-ed from a service provider may have a slightly higher bar to traverse into trust.
Exception: a long history of partnership with that service provider.
Depending on the investor and the relationship, this could work.
There has to be a clear reason why someone passed on the investment themselves.
If a firm only invests in software, and you’re a medical device, it’s pretty clearly not a fit. If you’re deep tech and they’re consumer products, it makes sense why the investor passed.
But know – in the back of every investor’s head is — “The Exception.”
If an opportunity is amazing enough, investors expect other investors to make an exception.
*EXCEPTION* EXAMPLE
Benchmark and WeWork. Benchmark didn’t do real estate. Until WeWork. Because Adam Neumann and his vision were so compelling, they made an exception.
Despite WeWork’s fall from grace, Benchmark made a 40x return. Exception validated ✅
Best way to get an intro to a VC in order of priority:
It seems counterintuitive.
Pitch the investors or firms you’re least excited about FIRST.
Save the ones that seem awesome or seem like a great fit for last.
🤔 Why?
You’ll be more cohesive, polished, confident, and prepared.
THAT’S what you want to show your preferred investors.
This comes from the Salesloft playbook. They raised $245M from top tier investors using the reverse order strategy.
There’s a reason the championship game is played at the end of the season. Save the best for last.
A well-rehearsed pitch is noticeably better. Practice lots. Like, hundreds of times.
(This is why you save the best investors for last!!! See #2)
To stand out even further, be excellent during question and answer time. This is what separates good from great.
How you answer investor questions can make or break your fundraise.
Check out —> this research to nail your objection handling.
If you do it right, you’ll raise 14x more money than your peers.
This raises the question…
PRACTICE TIP #1
Pitch meetings are like job interviews. You’ll get asked the same 20 questions over and over. (“Common investor questions” feels like a future post…) Different questions, same playbook.
ACTION: Make a list of likely questions. Plan your answers. Practice them aloud. Have a founder friend poke holes. Remember: promotion not prevention.
PRACTICE TIP #2
Go to Pitch Practice! It’s weekly. It’s free. It’s led by the awesome Jacey Cadet, VP of Marketing and Community at Atlanta Ventures. She’s fun, she’s brilliant, she creates a welcoming, safe, and entertaining environment to learn and practice.
Getting in front of someone in the industry for advice without burning an investor meeting is rare and game-changing. She’ll help your pitch and prepare you for typical investor questions.
ACTION: Sign up for Pitch Practice at the Atlanta Tech Village. Fridays at 1pm.
What other fundraising tips do you have? What is “common knowledge” in the VC world that founders may not know?
I sold to and managed relationships with enterprise customers at multiple companies. Every company was unique but certain patterns came up regularly.Here are 6 key strategies if you’re a startup selling to big companies!
Read MoreIt’s a great startup strategy to hunt deer. (See this classic Mark Suster blog about rabbits, deer, and elephants.)
Deer are SMB companies who can buy your software for ~$1,000/mo. They put on a credit card with no legal, no contract negotiation, and no collections.
It’s predictable cash every month with a short sales cycle.
Of course, elephants, I mean, large companies have problems too.
And they have a lot of money to spend on solutions…as long as they don’t trample you in the process!
I sold to and managed relationships with enterprise customers at multiple companies. Every company was unique but certain patterns came up regularly.
Here are 6 key strategies if you’re a startup selling to big companies!
IBM expects to pay $1 million dollars for your software. I don’t even know what your software is but IBM expects to pay that much.
If enterprise companies are your target market, make sure you charge enterprise prices!
All contracts with big companies go through Procurement. Procurement’s job is to save the company money. Procurement’s success is measured by how much they negotiate down a price.
Expect a 20% haircut from Procurement and factor that into your (already high because it’s enterprise - see #1) pricing.
Large companies expect to pay for software implementations.
They know they are high maintenance! #sorrynotsorry
Here’s what it will include:
It will take more time and people than you think. Plan ahead to cover your costs and provide a great experience.
If you do a big contract with a big company, lawyers will be involved.
Lawyers want to add value. They do this by redline-ing the crap out of the boilerplate contract and terms of service you copied from the internet.
You’ll want to make sure there’s no Goliath-vs-David funny business so you’ll get a lawyer too.
ICYMI: Lawyers are not cheap.
Every large company will ask for 24/7 support. This usually gets resolved amicably.
YOU: We offer support from 9a-6p Mon-Fri.
BIG COMPANY: Okay, fine.
Sometimes they really do need more support coverage. They should pay for that. (Theme of the blog . . .)
Once you price it out for them, they may realize that standard support hours are fine. Staffing for 24/7 support is expensive!
It’s also helpful to discuss who has access to support. Does every user have access or do they need to go through designated power users on their side before it gets escalated to your team?
Clarify upfront to prevent confusion, frustration, or excessive support tickets later.
Do Tips #1-5 make enterprise sound like a major headache? Are you throughly discouraged?? Fear not, my friends. There’s a less painful option at your finger tips.
Offer a month-to-month option that can be billed via credit card.
Most department heads can put a certain amount of spending on a credit card, no questions asked. At the very least, no lawyers or procurement asked. 😉
This strategy worked great at Rigor. A department within a Fortune500 company would sign on, paying monthly via credit card. Once we had internal traction and proven ROI, we’d start discussing a larger annual contract. Navigating the corporate approvals and negotiations went much faster. We also got fewer questions and concerns about our startup status.
Large companies can be amazing partners, fantastic marquee customers, and a huge revenue boost.
When startups move upmarket and start selling to larger customers, you’ll often hear:
It’s the same product with a different sales process.
Be prepared. Understand typical big company process and dynamics so you can align accordingly.
What tips do you have for selling to enterprise companies? What do you wish you would have known? Any strategies that have worked well for you?
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