Communicating Difficult Decisions: A Guide For Engineering Leaders with Q&A
A few months ago, I shared this guide for leaders who need to communicate a decision they disagree with to their team. This week, I spoke about this difficult situation that many of us run into throughout our career at O’Reilly’s Software Development Superstream “Becoming a Senior Software Engineer”. I loved the questions that came up during it, and want to share them, as well as my answers, with you.
Who should communicate what?
Q: Should I always disclose my opinion on a topic upfront with people?
A: Be strategic. Consider your audience, your role in influencing the decision, and your overall communication goals. Rushing to express a strong opinion can stifle valuable input from your team, as your authority can inadvertently shut down discussion.
If you’re speaking with your boss and you trust them, or someone asks you directly, you may want to share your own stance - maybe not all, all at once, or entirely unfiltered. Especially though when I communicate with people lower in the hierarchy than me or for broader communication (e.g. across teams or a whole department), I don't usually do that - I want to be thoughtful in my communication with them and because I'm in a position of power and people look to me for guidance, and my communication often has a large blast radius, I want to use that power wisely. I found for me, giving things a bit of time is usually helpful to get to more nuanced and thoughtful takes past first impulse reactions.
Q: How do you answer if a direct report asks whether you agree with the decision?
A: I definitely share to some degree at least often or when it's important to me, just not at all times and not all details. For example, I may share "here's the decision, here's a bit I'm a bit concerned about or disagree with", but also make sure to end on a somewhat optimistic note at least signaling that I'm still willing to go with it (otherwise I wouldn't be doing my job), e.g. "but I still think we can do it / it's worth trying / I'm curious to see / I may be wrong.” What I don't share is "here's a bit that my boss and I really fought about and I couldn't convince him, now I'm super frustrated about him because it seems like the data I presented wasn’t taken seriously, and you should be frustrated too." - Even if that may be true, one, my frustration will usually subside soon, and, two, I know this kind of detail isn’t going to be helpful for anyone.
Q: According to some tests, I could be a good leader, but I feel more like I am a trouble maker. How can I make my life easier? How do I move from a "troublemaker" mindset to a leadership one?
A: Start with introspection: Think about
whether you actually want to be a leader,
what being a leader means to you,
what it means to make your life easier, and
why that matters to you.
It also sounds like it would be really important to dive into what it means to you that you're a troublemaker, where and how that shows up, and what makes you behave that way: What are your motivations, goals, or impulses that make you cause "trouble.”
If genuine leadership is your goal, identify the leadership behaviors you'd like to embody and start practicing them in small, safe situations. This could be a helpful starting point to start changing how you operate. It can also be worth working with a mentor or coach to understand and break through patterns like these.
Q: When should a CTO or other high-level leader communicate big decisions directly, instead of relying on team leads as messengers?
For big decisions affecting (almost) all teams, I feel like the whole process could be simplified if the CTO or someone higher-up communicated the decision to everyone in a clear way (verbal + written with rationale). What do you think about that?
A: Ideally, both approaches are used! The CTO/CEO communicates the big picture, rationale, and importance. Then, team leads follow up, connecting that decision to specifics about how it will impact their team's day-to-day work. This approach balances top-down ownership with the personalized touch of a direct manager.
I agree, in my experience a combination of both is usually most effective for communicating decisions that affect a large portion of an organization/company:
The CTO/CEO or similarly high-up leader communicates the big picture, followed by
managers/team leads connecting with their teams more specifics about what it means for them.
That's usually a good combination of leaders taking ownership, while also empowering line managers and helping them tailor communication to the specific needs of their teams + reports, both of which are really important. The prerequisite to this sequencing of information is that managers/team leads are briefed beforehand; find more about this and a template in my playbook for managing in difficult times.
Navigating Disagreement as a Leader
Q: How do you convey information without getting frustrated when colleagues can't grasp what seems like a simple concept?
A: Frustration is understandable, and it’s human to feel this way. At the same time, it’s important to remember the simple yet sometimes difficult reality that other people don’t live in our heads, don’t see the world as we do, and what’s “simple” for us may not be the case for them. Most people don’t get up in the morning with the intention to do a bad job, and as a leader, it’s our role to help bring out the best in them. This also means that if people don’t understand things, it’s our job to adapt the tools and approaches we use to help them get there.
To help manage your own emotions, try shifting into a curious "detective" mindset: Focus on trying to genuinely understand where the breakdown happens. Phrases like, "Help me understand what's making this difficult for you" encourage non-judgmental discussion. Another technique is asking them to explain it back to you, which can help you identify points of misunderstanding; make this explicit to build trust and avoid that they feel like they’re going through an exam. Ultimately, you’re in this together, and the more you can own that, the faster you’ll get on the same page!
Q: What if the leaders above you in the hierarchy disagree with each other (e.g., your boss vs. your boss's boss)?
A: Avoid becoming a passive messenger or continuing the triangulation of mixed messages! Make the parties involved also part of resolving this as quickly as possible. Transparency is your best tool:
Talk to your immediate boss: "I'm currently a bit unclear about x, what I heard from you is y, but what I heard from bosses boss was z. Can you help me understand?", or "I understand direction X from you, but direction Y from your boss. Can you help me reconcile this?" Framing it first as "need to understand" instead of “you two are obviously disagreeing” is a small difference in wording, but can often help: Oftentimes, people aren't even aware that they're sending mixed messages, or it's a result of different levels of context or ways of expressing things. I’ve often worked with bosses that just had very different personalities and would use different verbiage, even when they were talking about similar ideas.
Push the transparency out: Email both parties, summarize what you understand to validate the path forward, and give both a chance to weigh in again if needed.
Repeat if necessary.
Handling Reactions to Unpopular Decisions
How can you reconcile your team's needs and emotions when the team is a cross-cultural one with different points of view and reactions to decisions?
A: You likely can't reconcile the differences in needs, emotions, etc. - and that’s okay! After all, those differences are also enriching a team (that doesn't mean they're always easy to handle). What you can get alignment on though is in acknowledging that these differences exist and are okay, and in defining together how to move forward: How to come together as a team to address the decisions/changes and move on from there. Focusing on that after some initial reactions and change resistance/responses can be really helpful. The rest in terms of individual change responses is more for 1:1s and work with individuals.
Q: How do you respond to emotional outbursts from team members when communicating a difficult decision?
A: I think it's important to make space for individuals responding differently, and acknowledge that that's okay, while also allowing that others may process things differently. It’s a fine line to walk between that and avoiding that it becomes only about the one person who has a strong reaction. Here are steps I find useful in such a situation:
Acknowledge: Describe what you observe without judgment, play back what you think you heard ("What I’m hearing from you is…”).
Ask: "How would you like us to proceed from here?"
Offer options (if needed): Suggest a short break if they're struggling to articulate a preference.
Set a reconnect time: Agree when to follow up.
Remember to respect individual processing styles while helping the team as a group process and adressing everyone’s needs, so there’s ultimately a path forward.
Q: How do you communicate a decision YOU support, but know the TEAM won't like?
A: Acknowledge your alignment, but prepare for a range of reactions. In this case, prepare even more clearly what your goal is and for a range of reactions. Brace yourself for some conversations that may be a bit difficult. Focus initially on understanding those reactions so you can give meaningful feedback to upper management. You'll likely need follow-up discussions about practical implementation. And hey, some team members might even come around!
Disagreement and taking action
Q: When do you know it's time to leave a company due to consistent disagreement?
A: It's a tough call, but in this context, you may notice a pattern of fundamental disagreement with leadership that is making your situation unsustainable. That’s the "thousand papercuts" scenario (many small but accumulating frustrations), or reaching a point where your values or ethics are so compromised that you can't stay in the role. It can also happen that the organization is making changes that are so drastic or of a natur that you’re not willing or unable to get on board with. Ultimately, as a leader and human, you still need to be able to look at yourself in the mirror, i.e., live with the decisions you’re making. That part is important too.
Remember, leadership is an ongoing journey of growth and adaptation. Even the most seasoned leaders grapple with communicating tough decisions. If you'd like to explore these leadership and communication challenges in more depth, you can also contact me for 1:1 coaching and mentoring.
