I recently spoke to someone working with a brilliant founder who was getting in their own way.

The founder wasn’t open to new ideas or different perspectives and it was hurting the company.

How do you reach someone who won’t listen or shuts down other people’s suggestions????

Replace “founder” with “boss,” “co-worker,” “my teenager.”

Or maybe instead of reporting to the founder, you are an investor (hypothetically speaking of course) who can’t “tell” someone what to do but wants gently steer in a positive direction.

Here are 3 strategies I’ve found helpful when working with strong-willed founders (or anyone!) — as a startup COO, tech investor, and general human being.

1. Ask lots of questions.

You almost never change someone's mind by telling them what to do.

But you can change someone's mind by asking them thoughtful questions so they realize what to do.

And think it's their idea.

There's a reason why therapists (and business coaches!) ask questions.

And it's not because they don't know the answer. 😉

Having someone else come up with the answer, say it in their own words, feel ownership, use their own wisdom — is wildly important for buy-in and change.

Furthermore, it’s possible that you don’t have the exact right answer. Maybe you don’t fully understand the situation or maybe they have an even better idea than what you’re thinking of.

Asking questions can uncover all sorts of brilliant solutions!

You know what the title of this section should have been???

• What happens if you ask more questions?

• What are good questions to ask?

• What helps change your mind?

See how much more fun questions are than directives???!!!!!

Did it trigger any great ideas?? 😉

2. Pitch it as an experiment.

If you know me, you've probably heard me suggest this before:

"Can you do it as a test?"

Yes, of course, at Atlanta Ventures, we love to run tests around business ideas (examples here and here).

It works for internal projects as well!

If you have a new idea or you’re hitting a lot of objections, instead of trying to change everyone’s mind, suggest an experiment.

“What if we try [XYZ] for [30] days? I could run a quick test doing [ABC] for [$1000] with the goal of [123].”

Designate a specific amount of time, money, resources, and what a successful outcome would be. Here’s a step-by-step process and template and a description of SMART goals.

It’s low risk for the business and — very important — the ego!

No one is directly challenged, no one is “wrong,” no one has to communicate a change in strategy.

It’s a low-key, short-term experiment with clear parameters.

Who doesn’t love to try new things and look at the results?

3. Frame it as “More”

A brilliant HR leader (hi Carey Bongard!) taught me this one…

Whenever possible, phrase feedback or coaching as “more”:

• Why are we pouring money into that dumpster fire? Let’s do more of what’s working well.

• Be less negative. Can you give even more positive feedback?

• Don’t focus on the details. Do more strategic, big picture work.

• You’re not communicating enough. Communicate more across the company.

• You are going rogue and it’s causing problems. More collaboration with the engineering team.

Humans are much better at doing more of something than less.

Feels abundant, expansive, and positive.

Especially good for someone who:

• reacts poorly to constructive feedback

• you want to influence and inspire in a positive way

• is your boss 😉

Do more “more”!

It’s Not Just For Founders

Spoiler Alert: these strategies work on direct reports, anyone in your organization, even family members.

In a shocking turn of events, most people don't like being bossed around and aren’t going to do what you say even when you’re right!

(I know. It was a terrible realization for me too. The world would be so much better if everyone just did what I say!!! 😜)

I should also be clear that there is a HUGE upside to that annoying stubbornness you’re dealing with.

It means someone has high conviction, they don’t give up easily, and they’re not swayed by others or peer pressure.

When dealing with humans, it’s always a mix of good, bad, and messy!

Just like a startup. 😉

Have you used any of these strategies? Do you have other tips for helping to shift a stubborn individual? Founders, have you ever been hard to convince?? 😁😉🙋‍♀️

I’d love to help more entrepreneurs! If you’re enjoying the O’Daily, please share with a founder or startup leader who would enjoy practical tips and #momjokes. 😁😁😁

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