Article

Managing Up: Creating Purposeful Conversations With Your Boss

You need feedback on your performance or a project, and the only person who can help you is your boss. How do you make this happen without wasting their time and energy?

Navigating the relationship with your boss can be one of the most challenging aspects of work—especially if you directly report to the founder of the company. Since your boss presumably has a lot on their plate and is busy steering the ship, it often feels safer to “wait and see” instead of requesting timely feedback. But playing waiting and guessing games is never the best option.

Instead, you can bridge the gap by anticipating some of the issue areas and bringing potential solutions to the table. To quote the motto of many founders and leaders: “Help me help you.”

This requires you to do two things:

1. Proactively ask for feedback on your performance frequently.
2. Hold your boss accountable to results.

Asking for feedback

In entrepreneurial organizations, processes and roles evolve constantly, so getting feedback once a year simply isn’t enough. Can you imagine only getting feedback from your customers once per year?

Finding success in your role takes continuous reevaluation. You want your role to make sense in the grand scheme, and you want what you’re doing today to have a direct impact on the success of the company in the long run.

At the same time, the founder’s focus is scattered across many goals and ideas. You see it in how priorities suddenly shift and hear it in team meetings. That’s okay! This is the entrepreneurial process of figuring things out and building the plane as you fly it.

But how often do you wish for a formal feedback process so that you can finally get a real evaluation? Or when you ask for feedback, it falls flat? (Ahem, “You’re doing great. Keep it up!”)

Learning to ask for feedback can take a significant cognitive load off of the founder and give you what you’re looking for. To maximize value, you need to reduce formality and get specific.

Reduce formality

You might not see it this way, but asking a founder for a performance review or general feedback can feel like a loaded request to them. They start thinking about performance management processes and consulting groups instead of what you probably want: a few minutes of feedback on a recent project, or how you can learn and contribute more to the organization.

Well, the lighter the lift, the faster and easier we learn. Yes, performance management processes are important, but organizations run more smoothly in the short term when feedback can be shared without bureaucratic formalities. For tasks affecting the daily and weekly processes of the company, you want feedback in real-time.

Here are a few ways to reduce formality:

• Set shorter, timeboxed meeting times for feedback. Ask your founder in advance that you want feedback—do not surprise them with an on-the-spot request!
• Send your questions in advance. (Read below.)
• Invite your boss to spend no more than five minutes preparing for the feedback. You can even have them do this at the start of your meeting in case they don’t have time in advance.
• Keep timescales small. Look at last week and last month, instead of last quarter or last year.

Get specific

Avoid generalities. When you ask general questions about your performance, it can be hard for leaders (especially new ones) to express what they want to say clearly, constructively, and (this is necessary sometimes) delicately. It takes time for founders to whip up “general” feedback, and we all know that time is a scarce resource. So, be specific about where you want feedback, and why.

Here are some tips and hypotheticals to help you guide the conversation.

Use quantitative measures.

If your boss is seriously time-crunched, use these questions to keep the feedback short, lightweight, and less personal. It’s results-focused instead of person-focused. And if there’s anything obvious to them that might help you raise your numbers, they’ll tell you.

Examples:

• On a scale from 1 (severe improvement needed) to 10 (crushing it), where would you rate my performance in the last week/month?
• What results am I creating that are lifting the score up??
• What results am I creating that are pushing the score down?
• What could I be doing to earn a 9 or 10?

Writing this down for yourself can further additional benefit you in two ways:

• It can aid your own self-reflection. What are the patterns you notice in the data points? What can you learn from it?
• It creates a paper trail. When it’s time for full-scope performance reviews, you have evidence of all the results you created throughout the quarter/year—which can help you justify more responsibility within the organization.

Get perspective on your strengths.

This is always a helpful path to improvement because the way you perceive yourself is often different from the way others perceive you.

Examples:

• What do you perceive to be my three personal strengths?
• What are three areas in which I could improve?
• What are three recent accomplishments I should be celebrating?
• What are three recent failures I should be learning from?

These questions tend to be best answered with time to reflect and write in advance—which your founder may not yet be ready for. Try reducing formality by choosing one and having a brief conversation about it. Actively listen and seek to understand.

Coach your boss to identify opportunities to help.

If your boss can invest more time into the process, you can gather more detail. First, ask yourself where you stand within the roles of your job. Where are you doing well? Where are you struggling? Ask for their help in identifying your blindspots. By acknowledging these factors, you can refine your questions and help your boss deliver more pointed feedback.

Examples:

• What are the major opportunities you see in the next six months?
• What’s currently keeping you up at night? (What are your major challenges right now?)
• What responsibilities need to come off your plate to help you focus more on seizing these opportunities and addressing these challenges?
• Which of these responsibilities could I (or my team) own in the near term?
• What would need to be true to increase your comfort with delegating this responsibility to me (or my team)?

These questions are focused clearly on solutions. They can either catalyze your boss to delegate further responsibility to you and your team, or help you both see pathways to building your capabilities for future delegation. Further, they can allow you to experiment, empower your team, and drive results.

Holding your boss accountable

It may seem like your boss lives in a world of constant chaos. As I mentioned above (and as you’ve noticed), there’s a lot going on for them. This is why having a shared vision and shared OKRs is so important: It provides context that allows our efforts to make sense in the grand scheme of things.

Regardless of the chaotic nature of the founder’s role, you can and should still help hold them accountable to their commitments, especially for work you need them to do in order to move forward.

Here’s how:

Be specific about the commitment.

Try restating what you understand from their directive or communication. For example: “Just so I’m clear, you’re agreeing to share your feedback on my proposal by Friday at 2pm using written Google Docs comments. Our goal is to either both feel comfortable in moving forward with the proposal or know what needs to be changed. Is that right?”

Set an agreed-upon date.

• “When do you think you’ll have this completed by?”
• “Do you see any risks in this deadline slipping?”
• “How can we mitigate the risks?”

Don’t let unaccountable behavior slide! If your boss committed to a date, and you need results to move forward, bring it up and (importantly) offer solutions.

Here’s a hypothetical scenario where your boss hasn’t done what they said they would do:

STATEMENT: “We agreed to a deadline of Friday at 2pm that you would have the feedback completed. I haven’t received it yet.”

IMPACT: “By not having the feedback, I cannot continue to the next phase.”

RESULT: “As a result, we risk missing our external deadline with our customers.”

OPTIONS: “Would you like to hear some ideas that we could entertain in order to move this forward?” YES/NO.

If YES, “To keep moving forward, here are our options…”

• “Skip feedback. Give me the go-ahead to continue without your feedback.”
• “Answer questions live. We talk through it for 15 minutes and we address your top concerns. If yes, let’s schedule a meeting.”
• “Take 30 minutes to review the work on your own and share written feedback. If yes, let’s set a new deadline.”

“What do you think? What would be helpful to you to move this along?”

Create more solutions, not more problems.

Diagnosing problems is helpful, but if you don’t combine action with awareness, it can create frustration. Telling a founder they didn’t complete something they were supposed to isn’t useful since they usually know this already, or they potentially forgot about the task.

Don’t just highlight the mistake. Offer help. By providing thoughtful potential solutions, you lessen their mental burden—you create a world where your boss can just “show up” and speak freely. Even better, by solving your boss’s problems and collaborating with them, you can improve in your role and stand out as someone with the company’s best interests at the forefront of your mind.

Reduce everything down to what you need. Get pointed. Get specific. Help your boss strategically think. How can you get the most out of them? How can you help them help you?