“My CEO Doesn’t Know…”

No matter the financial climate, there are always new startups established. Most of these startups are run by first-time founders. What do smart founders do? They often hire experienced leaders to help them (as opposed to trying to do everything in “hard mode”). However, I regularly encounter these executives who fail to leverage their experience to help the company. If you have more experience than your boss and find yourself thinking often, “the CEO doesn’t even know that X could be better,” this article is for you!

The Silence Trap

When you spot issues thanks to your hard-earned experience, you are doing precisely what the founders wanted and why they seeked out an experienced leader in the first place. Nevertheless, it is common for executives to notice these problems and fail to address them head-on.

Sometimes you feel like you just joined and that you need to give things more time to make sure you see them correctly, but then you become accustomed to the problems. Perhaps you fear being seen as a negative person or a complainer if you point out issues around you and prefer to focus on things “within your purview.” Another excuse I often hear is that the founders are not really interested in this feedback.

Having worked with many founders, I am sure of one thing: the founders worth working for are not thinking this. Give your boss some credit—after all, they were smart enough to bring you in, right? Most CEOs I talk to are actually lamenting how little their executive team is being proactive. You can and should speak up, but to do so successfully, you must keep a few things in mind.

First, be clear and make sure your message comes across. I sometimes hear CTOs describe how they had expressed concerns about an issue when in fact, the CEO never registered the conversation as a problem. Just like sometimes an employee doesn’t understand in a 1:1 meeting that you are not pleased and has to have that spelled out to them, the same sometimes happens with CEOs.

Second, take care of your own domain. Your words will have less weight if you seem capable of criticizing everyone without doing better yourself. Those leaders with a solid track record have much more cachet in exec team meetings.

Third, your ideas are more likely to be accepted if you have skin in the game and express your ownership rather than telling others what to do. Though not always applicable, it is always nicer to feel like the person suggesting the idea is willing to help execute it.

Common Issues

To drive this home, let us list some typical cases where we fail to leverage our experience. These are so common I came across each one in the last couple of weeks.

Lack of strategic thinking: If this isn’t your first rodeo, surely you’ve been burned in the past from unclear visions and poor strategic skills. About 80% of the experienced executives I talk to report their founders as being too myopic and not thinking big enough. The truth is that most people haven’t witnessed the acceleration a well-articulated strategy can provide or believe it is too cumbersome to do. You can help them take baby steps toward forming a roadmap that is shared with the company. Sometimes this means going from goals for the next month, to the next quarter, to a year, etc. Of course, you can also consider getting external help from an advisor that holds Sentient Strategy® sessions (this guy!).

Failing to create an executive team: Is your company a bunch of silos or a hotbed of innovation, creativity, and collaboration all across? Inexperienced founders frequently fail to treat their executive team as a forum that is just that, a team. They speak to them individually but do not focus on making them cooperate better. Providing examples of meetings that can be beneficial is a great way to start (for example, executives ought to be in planning sessions, or they’re not real executives). You can also start by taking the lead and establishing healthier relationships with your colleagues.

Peers not up to par: Perhaps the most challenging issue to tackle since this is not really your “role,” and it can feel like stepping out of bounds. Nevertheless, if you sense that someone on the executive team is holding the company back, you should be candid with the CEO. Sometimes, they never worked with a truly remarkable CMO or VP Product and, therefore, cannot even tell what they are missing out on. This has to be done with humility since you might not be privy to everything going on, but it is not an excuse not to voice your concerns.

These and other scenarios can be tricky, but you can get better at them. Two ways to get rapid improvement: hire me, or join the free Leading Edge Club—a closed global community for execs in tech to help one another.