Few management challenges are harder—or, often, more important—than managing up, particularly at the senior executive level.

There's this thing called the Peter Principle that states that "everyone rises to their level of incompetence"; that is, if you're good at your job you'll be promoted to the point where you're no longer good at your job. For many leaders, upward stakeholder management is among the first things that evidences this maxim's truth. And understandably so: by its very nature, upward-facing management is something that people don't see examples of until they're thrust into a role that requires it.

As people grow into more senior roles, they're often surprised to find how little structure, formal training, and even competence exists at those levels (often for the same reason as stated above). This is especially true at the very top in founder-led companies, making upward management in those cases even more critically important. Just as it's often harder to manage junior ICs than senior ones (the latter basically know how to self-manage, making the job much easier), the inverse is sometimes true at the very top in the case of founders who usually get to their positions with no regard to their management ability.

Advice for dealing with such situations overlaps significantly with the best practices for downward-facing management, but the pressures of interactions with higher stakeholders can often lead people to forget what's worked the basic management skills that have worked well in all other cases.

Psychological problem, psychological solution

Top leaders, especially founders, are under immense pressure. Their day is full of ambiguous decisions that carry massive potential for loss and gain, for themselves and others. Given that, it's surprising that founders aren't more anxious than they are.

Remember that they're just people, subject to the same kinds of emotions. I like to keep this mantra in my head as a way to stay on track when higher's anxiety rolls downhill. First, to understand and empathize with that anxiety. And second, to help fulfill my role as a leader to not let their irrational anxiety impact the team's psychological safety or our strategy. Nothing good ever comes of being reactive to emotion. Treat people problems with people solutions (management); don't change the product or your team to solve how they feel right now. Not only is it unfair, it's also solving what's almost always a short-term problem with a long-term solution. When, inevitably, the wind of anxiety blows the other direction, you'll have to change strategy again, causing the team and your company whiplash that's extremely damaging. Be an insulator and an interpreter between executive stakeholders and everyone else.

You can't solve what you don't understand—start there

It's important to lead interactions with executive stakeholders from a place of trust. I've never met one who wasn't incredibly impressive in some way. Very often, this way is their remarkable ability to predict what's going to happen, to intuitively understand the pulse. As Jeremy Irons' character (the CEO of a big bank) says in the great movie Margin Call, "I'm here for one reason and one reason alone. I'm here to guess what the music might do a week, a month, a year from now. That's it. Nothing more." Many CEOs and founders are better at that than anyone, and when you understand what that special sauce is about your exec stakeholder, you know what in them to leverage and how (and what tendencies to try to mitigate).

Slow down; don't rush

A key strategy to manage such feelings is to slow down. You don't have to know every answer immediately, or respond to every situation in real time. If you can control any variable, control "when". In this case, that means when you respond.

Confidence is key, but you're not expected to know everything

Leaders are hired for their judgement ability and management skills—not their ability to report information. When presenting to executive stakeholders, they're likely to ask you questions because they're curious to know the answer. It's not (or it shouldn't be) a test of your knowledge. The phrase, "I don't know that number off hand but I'll find out", is a powerful tool.

Storytime

As an example, there was one occasion (but this kind of thing has happened numerous times over the years) when a founder I directly reported to sent me an extremely critical series of messages lambasting my team's work.

Recognize what's happening: it's late, they're clearly anxious, and they're conveying that anxiety in the form of micromanagement. They're articulating a laundry list of problems they see in a feature we recently designed and reaching the conclusion that we must not have done sufficient research to support our designs.

Try to deconstruct their thought process. If the work is bad (as they believe) it must be for one of a few reasons. Either:

1. We're bad at our jobs (thankfully, we built enough confidence that this didn't seem to be the answer they reached for)
2. The process we've built was not followed as it has been before, or the process is insufficient to achieve a good outcome (this is what they concluded, placing the blame on the research phase)
3. They're (at least somewhat) wrong about their conclusions (nobody will reach for this when they're anxious)

In this particular case, as it is in most cases, it was a combination of the above:

• The designer that we had assigned to it was on the junior side, and a more senior one would have been more rigorous with ensuring stakeholder involvement. This founder knew that, but not why it was important that we assigned the task to him (we needed to build his confidence and experience and that can only be done if we give him challenges he will push his ability with).
• The process was actually extremely rigorously followed and we did outstanding research. In fact, funnily enough, it was this factor that meant that we discovered things that were actually contradictory to what common sense (including the founder's common sense) would tell us.
• The founder was wrong in concluding that the feature designs weren't research-backed.

Of these, the latter was the most important factor. How can we get him to that conclusion while he's angry, scared, and proposing radical changes at the last minute?

1. Slow down the interaction and take control of the situation ("There's a lot here—give me a few moments to read through what you've just sent").
2. A psychological problem (fear) requires a psychological response (reassurance that the situation is, at least now, under control). Mirror and label their emotions ("I can see that you're angry. Rest assured I'm taking this very seriously.")
3. You're not expected to know everything ("I don't have all the information about what happened here and this deserves a well-researched response. I'm going to investigate fully, but for now, let me tell you what I do know and what we're going to do next")
4. Defer the conversation to a time when you better control the terrain and hold more cards ("I'm going to get back in touch within the next few hours with full information once I've had a chance to look into this")
5. Follow up with a well-researched explanation AND, importantly, a plan of what to do next at the same time. I like to structure such a communication into direct bullets that people can easily digest.

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