What Founders Wish Their Execs Understood
Written by Dave Bailey
Written by Dave Bailey, Oct 22, 2026
Working with a founder is not the same as working with a traditional CEO. Founders hire execs for their expertise, then clash with them over unspoken expectations about vision, speed, and honesty. Here are the five rules that make or break founder-led leadership teams.
Key Takeaways
- In a founder-led company, the principle is: give people a vision and trust them to make it happen. Your first responsibility is to stay aligned with that vision.
- A founder’s intuition is a signal that they have context you don’t. You don’t have to follow it every time, but you do need to find out where it comes from.
- Communicate material changes as they happen, not at the final presentation. Use Empathise, Explain, Extend to manage the founder’s expectations.
- Founders operate on an accelerated timeline. Change the question from “How long will this take?” to “What’s the most valuable thing I can do that only takes 15 minutes?”
- Great founders are truth-seeking and hate politics. Deliver difficult truths constructively, separating facts from opinions.
As a founder, you play by a different set of rules to traditional leaders.
But if that’s true, your team’s rules must be different too.
So what does this mean for your leadership team?
Many of the frustrations between founders and their execs come from unspoken expectations about what it means to work in a founder-led team.
Even if you don’t agree with all these expectations, they should lead to a useful conversation.
I’ve written this piece for your leadership team. Feel free to forward it to them.
Five things to know about working directly with a founder.
1. Your Job Is to Make the Founder’s Vision a Reality
A founder hires you for your expertise.
“I don’t know as much about marketing as you,” they say. “That’s why I’m hiring you.”
So you come in with your vision, your experience and your ideas. You take ownership, as requested.
Six months later, the founder jumps in and vetoes some of the decisions you made. You feel disempowered and tell yourself the founder doesn’t trust you.
This is a common pattern in founder-led teams. But why?
A traditional leadership principle is: give people goals and trust them to figure it out their way.
In the failure mode described above, founders are trying to be “good leaders” and execs are trying to be “good execs”.
However, in a founder-led company, the principle is different: give people a vision and trust them to make it happen.
Goals can be written succinctly. For example, a goal might be moving a single number.
However, visions are full of important details. The idea that you can fit a founder’s vision into a sentence is completely wrong.
In addition, the vision of a high-growth company is subtly changing all the time. Founders are uniquely positioned to have the most context across the business.
So in the example above, the exec was probably trying to achieve the goal without fully understanding the founder’s vision.
Understanding this vision isn’t a single conversation, because visions are a moving target.
Your first responsibility is to stay aligned with the founder’s vision as you work to make it happen. That means being constantly curious about what the founder sees that you can’t.
The curiosity itself actually helps to clarify their vision, and your influence can help them update their vision.
Once you both have the same vision, you’re set up for success.
2. Surface Founder Intuitions and Take Them Seriously
Vision speaks to where you’re going, but a founder also has intuitions about how to get there.
There’s a quote attributed to Jim Barksdale, former CEO of Netscape:
“If we have data, let’s look at data. If all we have are opinions, let’s go with mine.”
I’d change the ending. “If all we have are opinions, make sure you understand mine.”
In a startup, you’re often deciding without data. When a founder has an intuition, it’s a signal that there’s information or context they have that you don’t. You don’t have to follow the founder’s intuition every time, but you do need to find out where it comes from.
I’m definitely not saying founder intuitions are always correct.
I remember being so sure about a particular email strategy that I bet my head of marketing that in an A/B test, my approach would win. She ran the test and won by a landslide.
I’d placed too much faith in a blog post I’d read about subject lines. My head of marketing knew our customers better. She was one of them.
Founders don’t want you to follow their intuitions blindly. They often throw out ideas and intuitions in the moment, while assuming that you’ll go deeper and take ownership of the choice.
A simple way to surface intuitions is to run your plan past the founder and ask for their intuitions. “Where do you think the weakest point is?”
Unfortunately, founders won’t always volunteer their intuitions, trying to be a “good manager”. Three months later they regret not voicing those intuitions.
That’s on them. But when curiosity comes from you, it’s safe for them to share without taking away your ownership.
3. Manage Founder Expectations as Things Progress
We often think about empowerment as having freedom to pursue your ideas. However, that freedom comes with a responsibility to keep others informed as your plans change.
This brings us to the third failure pattern.
You align on a vision for a project, and listen to the founder’s intuitions. Then you get to work.
Along the way, things don’t go to plan. Some of the founder’s assumptions were wrong, so you figure out something with a higher likelihood of success. And it’s not just one thing, it’s several things.
Then, after weeks and months of work, you present back to the founder for sign-off and feedback.
But the founder frowns and tells you they are confused. “I wasn’t expecting this.”
You leave feeling deflated, and the founder leaves concerned you aren’t on the same page.
In a founder-led company, the founder is holding a huge amount of context. You can imagine it like a giant spreadsheet in their brain with lots of linked cells between pages you can’t see.
It’s normal for scope and plans to change, but no-one teaches you how to communicate these changes with the founder.
Communicate material changes as they happen, rather than waiting until the final presentation.
I have a simple 3-step process for managing stakeholders’ expectations, and founders really appreciate it when you do this: Empathise, Explain, Extend.
a) Empathise First
When you communicate changes, confusion and even disappointment are natural reactions.
Leading with empathy makes the other person feel understood. But the only way to effectively empathise is to know what they care about and what they were expecting.
That’s why, in addition to understanding the founder’s vision and intuitions, you also need to understand what they care about.
Stating “I know you care a lot about X” before revealing why you needed to change it lets the other party feel listened to.
b) Explain Your Thought Process
Now you need to take them through your decisions.
A good way to explain your decisions is to state the goal, explain why the original plan didn’t work, explain the options you considered, and why you chose the best one.
Listing out options makes you come across as thoughtful, and removes the obvious follow-up: “What about X?” or “Did you consider Y?”
Showing the logic behind your decision can build trust in your decision-making process, even if they don’t agree with the decision.
c) Extend a Gesture
This separates the good managers from the great ones.
If you know what they care about, and what’s likely to work, there’s usually a way to include something they care about in the final decision.
For example:
- I know X is important to you, so we’re going to do Y.
- I know you care about X, so the next step is to do Y.
- One benefit of this approach is X, which I know is important to you.
Working something they care about into your decision helps them feel like you’re looking after their interests.
This process doesn’t just work with founders; it works with anyone whose expectations you need to manage.
4. Work to a Founder Timeline
In most companies, the default timelines to complete tasks are:
- By next week
- By the next meeting
- By the end of the cycle
However, in a startup, speed is your biggest source of competitive advantage.
That’s why founders often have different defaults:
- Immediately
- By the end of the day/tomorrow morning
- By Friday
For example, imagine you’re in a Monday team meeting and the founder mentions a board deck due the following Tuesday. They’ve requested a few slides from your area.
Eager to help, you say: “Sure, I’ll have them for you by our next meeting.” That’s next Monday, the day before the board.
The founder goes along with it.
But the following Monday, you learn the founder pulled the data over the weekend and built the slides themselves.
They realised they needed it sooner than expected.
However, in a high-growth company, this is almost always true. Founders operate on an accelerated timeline.
So if you want to succeed in working with a founder, aim for faster turnarounds.
This does not mean working more. It means changing the question from “How long will this take to complete?” to “What’s the most valuable thing I can do that only takes 15 minutes?”
Often, it’s a shitty first draft.
Shitty first drafts are a great way to build momentum and clarify expectations early. However, it’s critical they happen as quickly after the request as possible, so it’s clear you haven’t spent much time on them.
Waiting a week or two to share a shitty first draft can have the wrong impact, leaving the founder wondering why it took a week.
Manage your calendar so you have 15–30 minutes to react quickly to founder requests.
In a founder-led company, fast with feedback beats slow with disappointment.
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5. Reject Politics and Tell the Truth
I spend almost all my time with CEOs, so when I go to dinner with friends who are execs, it’s amazing to me how real politics is for them.
I’ll ask a naive question like: “Have you told them directly?”
They’ll then list all the reasons why they can’t tell the truth.
“My founder doesn’t want to hear the truth. They get angry when I tell them.”
This is the fifth failure pattern: execs hiding the truth from the founder.
But here’s the interesting thing. I speak to CEOs all the time about their team, and there’s one pattern so strong you can take it to the bank.
“I trust so-and-so because they tell me the truth.”
Great founders are ultimately truth-seeking, and they hate politics. Yet the advice you’ll get from other execs is to play the game and tell the founder what they want to hear.
In a founder-led company, this advice does not apply.
On the other hand, most execs are really bad at telling the truth. It’s an underpractised skill.
Founders are responsible for how they respond, too. But your part is to learn how to deliver difficult truths well.
When execs try to tell the truth, it comes off as negative or problem-focused.
Instead, people who are great at telling the truth do so constructively and with positivity, separating facts from opinions.
For example:
- Destructive: “This strategy isn’t going to work.”
- Constructive: “I want this strategy to work. There’s one assumption I’m worried about: X. Here’s what I’m seeing, and I have an idea for how to test it.”
Working in a founder-led company is demanding, but it’s also exciting because things move faster.
Bring your expertise. Be curious about theirs. Tell them when the plan changes. Move fast. And become someone they can trust with the truth.
And if you’re a founder sharing this piece, use it to start a conversation. Which of these ring true? What would you add? And what does your team need from you to make them possible?
These responsibilities are too important to leave unspoken.
Continue learning about founder leadership
- The Hard Truth of Working At a Startup
- Do You Trust Your Colleagues Enough to Say This?
- Write a Better Company Vision for Your Start-up
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Originally published Oct 21, 2026.
