Balancing your CEO, peers, and Engineering.

executive (39), management (203)

There are so many stories of hiring a new executive who comes in and wreaks havoc. I’ve seen engineering leaders start with a giant, doomed migration, marketing leaders who accelerate expenses until they necessitate a round of layoffs, and a number of executives fired in their first month. When people tell these stories, it’s almost always framed as a failure of the individual executives, but they happen so frequently that I believe there’s an underlying structural challenge in addition to individual missteps. Fortunately, this structural trap that snags many executives can be avoided by acknowledging its difficulties and navigating them with a deliberate approach.

When a new Engineering executive is hired, they are usually hired by a CEO who believes that the Engineering function is underperforming. When you talk to members of Engineering, they will have a different perspective, potentially that the CEO keeps changing direction too frequently. When you talk to peer executives and to the Board of Directors, there will be a third and a fourth narrative about what’s happening. Where new executives fail is that they think of these as opposing perspectives, when in reality they are all incomplete but valid slices of a complex situation. Successful executives debug these mismatched concerns until they merge together into a single cohesive perspective. Ineffective executives anchor on one or two perspectives and dismiss the rest.

In this piece, we’ll discuss these topics on building effective relationships that overcome this core structural challenge of being a new executive:

  • Understanding whether you’re supported, tolerated or resented
  • Navigating the implicit power dynamics
  • Bridging narratives across the CEO, Board, peers, and your function
  • Avoiding anchoring on previous experience
  • Fostering an alignment habit
  • Focusing on a small number of changes at a given time
  • Embracing transient conflict and preventing persistent conflict
  • Surviving a panicking peer executive

After working through these topics, you’ll have a clear roadmap for debugging the mixed messages inherent to operating as an executive, and an approach for building durably healthy relationships that support you through your entire tenure.

This is an unedited chapter from O’Reilly’s The Engineering Executive’s Primer.

Are you supported, tolerated or resented?

It’s obvious to say, but the most effective executives are proactively supported by their peers, the CEO, and their functional team. This is not the common scenario where members of the executive team operate in isolation within their functional spheres, and it’s very different from environments where some functions maintain a long-running animosity towards one another.

There’s no status website to check your relationship with other parts of your company, but it’s reasonably straightforward to figure out:

  • Supported is when others proactively go out of their way to make your efforts successful. For example, if you push for a monolith to services rewrite, they’d come to you with concrete concerns for why this might not work out, and ideas for how to adjust your approach.
  • Tolerated is when others are indifferent to your work. For example, they hear about your services rewrite, and pull any related work tickets into their sprints, but don’t make an effort to flag structural inefficiencies in your approach.
  • Resented is when others view your requests as a distraction from their actual work. For example, they’ll advise their teams to ignore your migration tickets until you escalate loudly.

If you’re already supported by most executives and functions you work with, then you’re in an excellent place and can stop reading now. If you’re not sure, or suspect you’re tolerated or resented by some functions, then read on to unpack the most frequent causes of damaged relationships and how to resolve them.

Even if you’re an executive who prioritizes supporting your team, it’s very hard not to come into your new job anchored on your CEO’s evaluation of how Engineering is performing. This is natural because you’ve just spent the entire interview process speaking with the CEO, and the CEO is your boss: if you don’t impress them, you’ll get fired. However, CEOs only hire new executives when there is a problem to solve, which almost always means they’ve been telling you all about Engineering’s problems, but they’re probably not telling you about everything going well, and their diagnosis of the problem may have some gaps.

You should listen closely to the CEO, the Board of Directors, and your executive peers’ perspectives, but don’t close your mind to other new perspectives. Just because Engineering is having problems doesn’t mean Engineering is the problem, and you’ll want to dig in with the team directly before switching from listening to problem solving. To be fair, Engineering is almost always part of the problem, but they are rarely the entirety.

Executives who underestimate the impact of these power dynamics are prone to treating the top-level symptoms as if they are the underlying causes, which leads to superficial and often misguided solutions. When you look at all the executives who quickly mandate widespread migrations or initiate reorganizations, underneath the decision is almost always this sweet siren’s song of power dynamics that misleads them to dismiss the input of the people doing the actual work.

While I certainly don’t recommend ignoring your CEO–they are indeed your boss–you’ll serve them more effectively by listening widely before you solve their problem. Moving with urgency to address symptoms rarely gets you closer to solving the problem that your CEO truly cares about.

Bridging narratives

The most talented executives I’ve worked with have a remarkable skill to weave four or five seemingly incompatible perspectives into a unified understanding. For example, Product might feel Engineering is slipping on delivery. Engineering might feel that Design keeps changing requirements. Design might feel that Product is making late but reasonable change requests, but that Engineering is intolerant of their change requests. Sales might believe that Engineering is missing all their committed dates because they’re not customer-oriented. The simplest explanation here is that Engineering is struggling to execute effectively, but there’s undoubtedly a more nuanced diagnosis that goes beyond casting blame, and that nuance will make it much easier to identify an effective solution.

When you run into a complex problem, slow down to bring many different perspectives into consideration before you push to solve the problem. When you get good at this, it doesn’t take much more time, and rather speeds up problem solving by skipping the contentious debate around assigning blame.

Executives who practice this skill of bridging narratives are acting as company-first problem solvers rather than operating from a place of loyalty to the function they lead. This leadership creates a culture–and expectation–of cross-functional partnership, and is the most effective way that I’ve personally found to build supportive relationships across functions and executive peers.

Don’t anchor on previous experience

Many new executives accidentally alienate their peers and functions by assuming their new company will work the same way that their old company worked. This is particularly common when senior leaders at large companies transition into smaller startups. Those leaders are conditioned to an unnatural degree of support and resources, which simply don’t exist in smaller companies. Simply by running their familiar executive playbook they can easily alienate their new colleagues.

Avoid this by watching how others solve problems in your company and then asking them why they solved them that way. Some executives think it’s faster to learn by running into walls, but I’ve found that to be ineffective when those so-called walls are in fact your coworkers. No one appreciates being run into, and it creates a lasting impression that you’re focused on yourself rather than operating as a member of a collaborative executive team.

Fostering an alignment habit

Many executives assume feedback will come to them if they make mistakes. This is eventually true, but you’ll get the feedback much later than useful. You should instead build a habit of inviting feedback and making sure you receive it well.

This might be reaching out to participants in an executive meeting to ask if there’s anything you could have done better, or should not have done at all. Much of the time you won’t get any meaningful feedback, but occasionally you will. When you do get feedback, even when it isn’t particularly helpful, say thank you and ask a follow up question to better understand the feedback. When possible, ask narrow questions like, “Did I ramble a bit when I shared my perspective about reducing bonuses?” which are much easier to answer than open-ended requests for feedback. Most importantly, strive to reward feedback by actually improving on the things that are mentioned.

You don’t need to do this all the time with everyone you work with, but make a deliberate effort to occasionally ask everyone you work with closely. You should always be asking for occasional feedback in order to ensure folks have an opening to share.

Focusing on a small number of changes

Each time you come to colleagues with an idea, they refer back to their mental list of the last few ideas you brought them. Did those ideas go well, and did they end up feeling good about them? Are those ideas still ongoing without clear resolution, did they end inconclusively, or did they end up being viewed as a waste of time?

As long as your previous ideas have been effective, then folks will generally be glad to support your next batch. If they haven’t gone well, then they won’t. Consequently, your best bet to retain the support of your team and peers is to focus on delivering a small number of changes with meaningful impact. Don’t be the executive who pushes a number of technology migrations before finishing the first one. Don’t be the executive who claims to rework the planning process without ever using that new process.

Pick a few things that you’re confident will work, and deliver them. This is obvious advice, but it’s often ignored, and ignoring it will quickly get you placed into the tolerated or resented buckets.

Having conflict is fine, unresolved conflict is not

Many executives aim to eliminate conflict in their working relationships, which I believe is subtly the wrong goal. Real companies experience rapid changes as they grow and the markets they operate in shift. If you’re experiencing zero conflict day to day, then it’s very likely that you are ignoring conflict rather than resolving it.

Conflict isn’t inherently negative: experiencing new kinds of conflict is an important sign of growth. The sort of conflict that you want to avoid is unresolved, recurring conflict. An example of healthy conflict is an executive team who disagree on implementing a return to office policy. This is a complex topic with a number of different perspectives, and you want to surface all those perspectives enroute to deciding on your company’s approach. An example of unhealthy conflict is an executive team who strongly disagree on the size of relative investment between Research & Development (R&D) and Sales & Marketing (S&M), and who continue arguing without alignment each time they revise the financial plan.

When you detect an unresolved conflict, spend time understanding the different points of view and why they aren’t able to agree. Much like the challenge of finding a unified narrative that spans CEO and functional perspectives, there is usually a unified view that acknowledges seemingly opposing perspectives. If you can find it, you can often untangle the conflict. If not, it may be time for your executive team to establish a clear escalation mechanism to explicitly resolve points of conflict.

Finally, keep an open perspective on whether you are the person preventing conflict from resolving. Sometimes I’ve gotten so attached to my own perspective that I couldn’t let things go, even when it wasn’t particularly important, which always ended up causing more harm than it was worth. Even if you disagree, it’s still worth letting most stuff go to keep the executive team healthy.

Surviving peer panic

Sometimes things go awry even if you build effective relationships within the company. The most frequent version of this is when one of your peers starts to get negative feedback from the CEO, and that peer struggles to incorporate that feedback effectively. This is particularly messy to deal with as a newly hired executive, who is trying to build a relationship with a peer who’s more focused on short-term survival than building a long-term relationship with you.

Some examples of this happening:

  • Engineering executive is held accountable for slow delivery, and switches to blaming Product for frequently changing feature roadmap
  • Sales executive is held accountable for missing quota, and switches to blaming slow Product and Engineering delivery
  • Marketing executive is held accountable for high customer acquisition costs, and switches to blaming Engineering delivery on a marketing website

When this happens, try to find empathy for the individual who is struggling to address the concern, and then sit down with them to try to solve it together. Your peers will sometimes struggle, and sometimes they will point blame towards you, but ultimately succeeding as an executive team is a group activity. Even if an executive is performing poorly today, it’s usually less disruptive for you and the company to improve that executive’s execution than to find and hire someone new. Even if you aren’t ultimately able to help this particular peer succeed, you’ll come away with a clearer understanding of how to support their replacement.

At their worst, these situations get pretty unhealthy, particularly if the CEO has written off an executive but doesn’t have a concrete plan for exiting the executive from the business. The longer this goes on, the more uncomfortable it will get. At that point, push your CEO to make the change, and insert yourself as a buffer between your team and the panicking executive. Until your CEO cleans up the mess, you can at least minimize the disruption on your team.

Summary

At this point, you have a clear framework for becoming, and remaining, an executive supported by your peers, your CEO and your team. Continue to invest in your relationships. Continue to find the overarching perspective that merges the seemingly incompatible views around you. If you’re ever uncertain what to do, search for the approach that maximizes your impact at the company over the next three years rather than the next three months, and do that.