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Estimated reading time: 4 minutes
While your leadership journey will be full of high points, you should expect at least a few lows to hit as well. Here’s how to manage them.
The highs and lows of leadership can feel like a rollercoaster. The highest peaks can feel like you’re on top of the world after reaching a major milestone, seeing people grow, and receiving great feedback about your team. On the other hand, the lowest lows can lead to sleepless nights and distracting thoughts as you navigate uncertainty, difficult conversations, and disappointment.
Let’s cover a few strategies to help you manage the emotional dips as you ride your leadership rollercoaster.
Focus on what you can control and influence
Stoicism encourages us to focus on things we can control and influence. Although we might spend time worrying about how others will respond or react, seeing the world through the Stoic lens reminds us that we can only influence reactions.
Imagine, for instance, delivering difficult feedback to a team member, and you’re worried about how they will react. You can’t control their reaction, but there are some steps you can take to increase their receptiveness. Avoid sending feedback via email or Slack/Teams messages where there’s not much room for context. Before sitting down, let them know you’d like to offer some feedback and ask them to pick a time and place where they can discuss it. Giving them a choice in where and when to receive feedback increases the chances they’ll be able to process it without a strong emotional reaction.
Similarly, let’s say your product counterpart decided to significantly change priorities without consulting you first. You’re upset that your perspective as an engineering leader wasn’t considered, but you’re worried that confronting them will disrupt your working relationship. You constantly debate in your head whether or not you should simply “live with it” or “challenge them.” Again, although you can’t predict how they will react to your words, you can certainly influence the situation by carefully picking your words.
Rather than focusing on them and guessing what their intentions were, focus on what you experienced, your perspective, and describe your need from them. For example, “Last week I noticed I wasn’t involved in the change in team priorities and felt disappointed and caught off guard. I have a strong need for inclusion and collaboration, especially around decisions that shape what we work on. Would you be willing to include me in future conversations about priority changes that impact the team?”
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Talk it out
When it comes to difficult conversations and navigating situations, fears amplify the more we keep them in our heads. The best way to address it? Talk it out.
When I’m coaching CTOs, they’ll often talk through a situation they are worried about. I ask them to explain their worst fears. Once they’ve done so, I then follow up by asking if they truly believe their fears will manifest. They often answer with, “Now that I’ve talked about it, probably not.” By talking about the situation out loud, they realize they were focused on the most unlikely scenario, blowing a situation out of proportion.
It’s helpful to ask a peer or mentor to walk you through a simulated conversation to help you practice your delivery. For example, let’s say you have to deny a team member a promotion they were hoping for. By rehearsing your word choice and demeanor, you become more prepared for such tough conversations.
Hope for the best, plan for the worst
Good leaders know that nothing ever goes perfectly. Listen to Eisenhower’s words, who once said, “Plans are worthless, but planning is everything.” Although we can’t control the future, we are better prepared to handle mishaps when we anticipate them.
For example, I remember working with a client who had a hard deadline to launch an ambitious project at the start of summer. The deadline was non-negotiable, and the campaign was immense. It felt impossible in the moment, but we put together a plan of action anyway.
Our plan showed, early on, that not all of the items on the client’s wishlist were possible to attain by the deadline. So, we pivoted. We presented them with some options about what we could do, such as increasing the team size or splitting the scope into pre- and post-launch phases. Both options had tradeoffs concerning extra budget or functionality, but these were at least plausible options we could discuss early on. Our client decided to split the scope rather than burn through the budget, and we were relieved we had a reasonable plan to hit our summer deadline now.

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Conclusion
The key to riding the emotional rollercoaster of leadership is not to avoid the highs and lows, but to develop strategies to manage them. By focusing on what you can control and influence, talking through your challenges, and planning for uncertainty, you will be able to get more sleep and lead more confidently.