Your Founder Hired You to Lead — So Why Won’t They Let You?

For more than a decade, founder-led companies have returned more than twice as much to shareholders as companies that are not founder-led, according to Bain. In tech, the multiple is higher still. The executives I speak with take roles at founder-led companies because they’re attracted to high returns. Then they discover the founder will not let go of the work the executive was hired to lead.

I coach C-suite executives who report to founders and co-founders, including COOs, CPOs, CTOs, chiefs of staff and heads of function. I also coach founders themselves, at companies ranging in size from a handful of employees to publicly traded behemoths. Most managing-up advice, my own included, assumes your boss holds a particular role, but this advice doesn’t stick when your founder is running a company they built themselves.

1. Test what your founder will actually delegate

Every founder keeps a short list of tasks they will never hand over, no matter what the organizational chart says, and some of those tasks are likely on your job description.

I worked with a chief of staff who reported to a founder. In interviews and in their job description, they were told they would own strategy, operations and business development, but they quickly learned that they didn’t truly own them. Sure, they could have fought for the scope they were promised, but it would have been a losing battle. Instead, I coached them to focus on projects where they had real ownership.

Delegation can break down in the opposite direction, too. A COO I worked with ran board meetings but was never asked to manage board relationships or investor conversations. Her founder kept those tasks close to the vest. At the same time, he handed over responsibility for the entire budget to her and took little interest in even reviewing it. Through our coaching, she decided to loop him in more than he wanted and used the board meetings as a way to connect with board members and investors.

Ask your founder what they want to stay close to, then watch what happens over the next quarter. Ask again as the company scales, because the list will likely move. What a founder says they will hand over and what they actually hold onto are not always different.

2. Map your founder’s inner circle

Nearly every founder-led company has a small group of friends and peers whose input carries weight. They often look like co-founders, early employees, board members or an executive assistant who has been there since the start. In some cases, this group includes a family member with no formal ties to the company other than being related to the founder.

Over the years, I’ve coached clients to look far beyond the org chart when thinking about how to get things done. We spend sessions creating their own map of key individuals who influence the founder, both formally and informally.

In your first 90 days of a new job, it’s important to take special notice of whose wisdom your founder repeats and whose objection changes their mind. Build relationships with those people before you need them.

3. Translate your founder’s thinking for your team

How a founder talks is often different from what they mean, and the translation depends on which type you are working with. I’ve seen two communication patterns come up repeatedly.

Visionary founders think out loud. They express a half-formed idea in a Monday meeting, but your team hears it as a mandate. They reprioritize their quarter unnecessarily around something the founder has already moved past, and your team ends up spending a weekend building a deck nobody asked for.

Conversely, operator founders speak in specifics. When they ask a passing question about a metric, your team should get to work and make sure they have the information they want. These founders mean what they say, and you need to listen.

In practice, this requires you to get clear on the type of founder you’re working with, as well as what they want from you and your team. You want to know whether an idea is just an idea that can stay half-formed or a real ask that requires action and follow-through. To find out, you need to ask directly.

4. Know when the mismatch is structural

Founder-led companies operate differently on purpose, which can make the signals of a toxic culture difficult to diagnose.

I coached a COO who never expected to work 40-hour weeks. She wanted something closer to 60. Her founder worked 80 to 100, without vacations or days off, and expected the same from his direct reports, because that is what he asked of himself. He expected her to care about the company as much as he did, without the equity that would have made that expectation reasonable.

I helped my client clarify whether this level of effort was due to a temporary build phase or his standard operating model. I also coached her to test whether she could keep up. It turned out that this was his standard operating model, which wasn’t anywhere near sustainable for her, so she ultimately left for a company that was a better match.

If you are trying to work out whether you are in a difficult stretch or part of a true mismatch, the following questions can help:

• Has anything moved from your founder’s list to yours since you started?
• Are decisions you make remade after you leave the room?
• Is your actual scope smaller than what you were hired for, and has anyone said so out loud?
• Is there anyone who can tell your founder no and be heard?
• Are you being asked to care as much as your founder, without the ownership stake that would justify such devotion?
• Would a different person in your seat hit the same walls?

That last question tends to be the most helpful. If the answer is yes, you’re looking at a structural issue, and trying to adjust on your end won’t change it.

Final thoughts on reporting to a founder

Reporting to a founder often asks more of you than reporting to a typical manager. Test what your founder will actually delegate, map the people they listen to, translate their words before you or your team acts on them and stay honest about whether the mismatch is a stretch or a structure. The executives who do this well build real scope within the space their founder leaves them. You’ve got this!

For more than a decade, founder-led companies have returned more than twice as much to shareholders as companies that are not founder-led, according to Bain. In tech, the multiple is higher still. The executives I speak with take roles at founder-led companies because they’re attracted to high returns. Then they discover the founder will not let go of the work the executive was hired to lead.

I coach C-suite executives who report to founders and co-founders, including COOs, CPOs, CTOs, chiefs of staff and heads of function. I also coach founders themselves, at companies ranging in size from a handful of employees to publicly traded behemoths. Most managing-up advice, my own included, assumes your boss holds a particular role, but this advice doesn’t stick when your founder is running a company they built themselves.

1. Test what your founder will actually delegate

Every founder keeps a short list of tasks they will never hand over, no matter what the organizational chart says, and some of those tasks are likely on your job description.