The Founder vs. Hired Executive Gap

Miscommunication is an odd thing. When you are used to writing a lot every day—but in code, not prose—you get used to thinking that words are easy. You write something and the compiler understands precisely that (unless you have a bug, of course). If only things were as easy when we have to talk to our fellow humans. I’ve seen heated discussions about work be dissolved in a minute when someone decided to write their suggested approach in pseudo-code and move the discussion to that level. All of a sudden, everyone in the room understood what was being said. We carry little compilers in our heads.

What do you do, though, when you need to talk about things that aren’t technical? I have all my clients rate themselves on a bunch of traits so we can pinpoint areas of interest to focus on. One of those traits is Communication: do your conversations regularly end with you understanding what the other party wanted to say and the other way around? Unsurprisingly, many find this as an area that needs improvement. One widespread use case is a communication gap that seems to exist between startup founders and their hired executives. Even people who used to work together in the past seem to have issues. In this article I want to list out some of the reasons for this and communication approaches that my clients have found successful for bridging this gap.

Mind the Gap

First things first, both parties have to understand that different perspectives need to be accounted for. For example, as a cofounder looking to hire a VP of Engineering, it’s crucial to visualize the way candidates will view the position and the challenges that come with it. Especially important are the ways in which this view is likely to differ from the way the founders consider it. I don’t claim that everyone is the same, and of course, there are outliers, like those executives who are very entrepreneurial. Nevertheless, the gaps I’ll list below seem like good rules of thumb to start with and then adjust.

Being aware of this allows both parties to spot areas where they should likely put in more effort in communicating clearly, expressing their thought process and priorities, and thinking outside their own boxes. In coaching founders, I’ve found that making this gap tangible helps them immensely when coaching their executives. On the other hand, executives who realize these attitude changes can often “manage up” better.

Risk Aversion

This is one trait that many think they grasp, but it runs deep and takes an honest effort on both ends to grok how the other views things and communicate it clearly. First, I imagine that it goes without saying that cofounders tend to be less risk-averse than employees, no matter how early they join the company.

Risks are often a big tension point between executives and founders. The founders seem always to want to step on the gas pedal, and the executives fear that going so fast will make the organization crash. One way of bridging this gap is to define the importance of different milestones and goals directly. The CEO who wants to invest time in an innovative and risky direction might consider this the core vision for the company. Therefore this will require substantial long-term investment and resources. On the other hand, it might just be another experiment, and the CEO is well aware that it might fail. The deadlines and attention for both scenarios are entirely different.

However, executives’ risk-aversion tends to treat both situations with the same point of view: putting in place a plan that all but guarantees success. It doesn’t make much sense to create all of these buffers and changes in priorities for something that’s only another experiment.


A large portion of cofounder CTOs I’ve worked with in companies of over 100 employees have stopped being “CTOs.” Their titles don’t really mean anything—if they see a problem they have an advantage in solving, they jump at it. This boundless agency is not something that usually transfers to executives. They treat their titles and role definitions more rigidly.

This rigidity has its benefits, clearly. Nevertheless, it can lead to the creation of silos, issues falling between the cracks, and general corporate slowness. Founders have the relative freedom to do as they see fit. I’ve worked with many founders that treat their executives similarly—they provide maximal autonomy, and all the executives need to do is take action. They are then surprised when their executives fail to do so. They wonder, “Why do I have to ask explicitly?”

Realizing that boundaries, like deadlines mentioned earlier, have varying degrees of rigidity can help us in helping people exercise the autonomy that we bestow upon them. In The Tech Executive Operating System, I devote a whole chapter to the concept of moving upstream as executives. It can be a lot easier to do so if the cofounders lend you a hand.


This one can be very elusive to spot. Examples I’ve seen recently can be where the CTO wonders why something hasn’t changed yet. The VP reports having talked to their peers several times—things within their purview are moving in the right direction, but other parts of the company aren’t aligning. The CTO, frustrated, eventually steps in and makes the same ask. Things work. The CTO walks away, muttering, “I have to do everything by myself.”

These situations are often not the result of a VP that doesn’t want to do the work. Things just naturally receive more attention when one of the cofounders asks for them. If we don’t realize this, we might focus on the wrong things. This is why I suggest smaller startups engage cofounders in hiring key talent. The CTO/CEO might be eager to free their time now that they have a VP, and I get that. But there’s no denying that with today’s market, people want to feel they are wanted, and part of that attention comes in the form of a cofounder talking to them.

Realizing that things sound differently depending on who says them is another element in this gap that we should become aware of. The compounding effect of treating this gap better across the company’s executive team can make a world of difference as your startup scales.