Managing upwards: How to lead when YOUR boss is the problem

Hey team good morning,

I cannot tell you how highly requested today’s topic has been, so I’ve spent the last few days researching, and pulling together my thoughts and experience around managing UP.

Because let’s be real, even though I always want to be super accountable, it’s not always us that’s the problem.

Sometimes, the very person who’s supposed to support you is actually the one making it harder. Whether it's micromanagement, indecision, lack of communication, or just plain incompetence, dealing with a difficult boss while trying to lead your team feels like fighting a battle on two fronts.

But here's the truth: you can lead effectively even when the leadership above you falls short. It starts with managing upwards - a skill few talk about but one that can make or break your success as a manager.

In this post, we'll break down what managing upwards actually means, how to protect your team while keeping your sanity intact, and the practical steps we can all take to lead when your own leader is dropping the ball.

What Does Managing Upwards Actually Mean?

Managing upwards is the art of influencing your boss to create a better working environment for you and your team. It’s not about flattery it’s about clear communication, setting boundaries, and filling the leadership gaps left by your manager.

Think of it this way: If your boss is the roadblock, managing upwards is building the detour. You’re not trying to replace their role, but you are ensuring the job gets done despite their shortfalls.

The Reality: When Your Boss Is the Problem

Let’s paint the picture with a real-world example. Sarah, a first-time manager in a tech company, found herself stuck between her high-performing team and her indecisive boss. Every project required multiple rounds of approval, and deadlines were constantly missed because her manager couldn’t make timely decisions.

“It felt like I was babysitting upwards,” Sarah told me. “I spent more time chasing sign-offs than actually managing my team. They were frustrated, and I was exhausted.”

The solution? Proactive upward management. Here’s how to do it.

Step 1: Identify the Leadership Gap

Start by getting clear on the specific ways your boss is falling short. Ask yourself:

• Are they micromanaging, slowing down progress?

• Are they distant and disengaged, leaving you without direction?

• Do they lack decision-making skills, causing project bottlenecks?

• Or are they unpredictable, changing priorities constantly?

Once you’ve pinpointed the issue, you can strategise how to work around it much more clearly.

Example: If your boss is indecisive, don’t wait for them to make the call. Instead, present options and recommend the best course of action: “We’ve got three paths forward - I’d recommend Option B because it aligns with our timeline and budget. If I don’t hear back by Thursday, I’ll move forward with that plan.”

Step 2: Set Boundaries Without Burning Bridges

A common trap managers fall into is overcompensating for their boss’s shortcomings. While it’s tempting to pick up the slack, it’s not sustainable.

How to Set Boundaries:

1. Protect Your Time: If your boss constantly dumps last-minute tasks on you, set clear expectations: “I’m happy to take this on, but it will mean pushing back [other task]. Which one should I prioritise?”

2. Limit Back-and-Forth: If you’re stuck in endless loops of “can you clarify this?” emails, suggest a weekly check-in instead.

3. Clarify Roles: If your boss is stepping on your toes with your team, have a direct (but respectful) conversation: “To avoid mixed signals, can we agree that I’ll handle feedback for my team? I’ll keep you updated on progress.”

Example: One manager I coached, Liam, had a boss who constantly bypassed him, going directly to his team with instructions. Liam solved it by creating a shared project tracker, ensuring all updates flowed through him first. It subtly re-established his leadership without confrontation.

Step 3: Speak Their Language

To influence your boss effectively, you need to frame things in terms they care about by aligning your communication with their priorities.

• If they’re numbers-driven, present solutions with metrics: “If we go with Option A, we’ll cut project time by 20%. Option B will cost more but reduce risk by 40%. What’s your preference?”

• If they’re risk-averse, emphasise stability: “This approach follows our existing process but solves the current bottleneck.”

• If they’re image-conscious, tie your proposal to their reputation: “Approving this now ensures we hit the deadline and present a polished update to the leadership team.”

Pro Tip: Pay attention to how your boss communicates. Do they love quick bullet points in Slack? Formal emails? Mirror their style to increase responsiveness.

Step 4: Shield Your Team - But Don’t Hide the Problem

Your team shouldn’t suffer because of your boss’s shortcomings, but it’s also important they understand the context without feeling demotivated.

What to Do:

1. Filter the Chaos: If your boss is constantly changing priorities, consolidate their asks into one streamlined message: “Leadership has shifted focus to X this week. Let’s pause Y and revisit next sprint.”

2. Be Transparent… Selectively: You don’t need to vent about your boss’s incompetence, but you can acknowledge challenges: “We’re still waiting on final approval - thanks for your patience. I’m pushing for clarity by end of day.”

3. Escalate Wisely: If the issue is seriously impacting your team’s performance, escalate - but with solutions, not complaints. “We’re blocked on X because of delayed approvals. Can we agree on a faster sign-off process for future projects?”

Example: Emma, a manager in a creative agency, had a boss notorious for last-minute project changes. To protect her team’s time, she started running weekly project planning meetings, locking in priorities. When her boss tried to swoop in with new requests mid-week, she could confidently say, “We’ve already allocated resources - shall I bump something else, or can this wait until next cycle?”

Step 5: Build Your Own Support Network

When you’re stuck under a difficult boss, having peers, mentors, or even external communities can be a game-changer.

• Find Allies: Build relationships with other managers in your org - they’re likely dealing with similar challenges and can share what’s worked for them.

• Get a Mentor: If your boss isn’t providing guidance, seek it elsewhere - whether through an internal mentor, leadership coach, or external network.

• Document Everything: If things escalate, having a paper trail of decisions, requests, and project progress protects you.

Step 6: Know When It’s Time to Walk Away

We can do everything in our power to help solve this problem, but I need to remind you…

We only get a very short time on this earth.

If your boss is actively harming your career, your team, or your mental health, it might be time to escalate or move on.

Signs It’s Time to Escalate:

• Your boss’s behavior is affecting project outcomes.

• They’re creating a toxic work environment.

• You’ve tried managing upwards with no success.

How to Escalate Effectively:

1. Stick to facts, not emotions.

2. Highlight the business impact, not personal grievances.

3. Offer solutions alongside the problem.

Final Thoughts: Lead, Even When Leadership Fails You

Managing upwards isn’t about fixing your boss. But it’s about creating the conditions for your team to succeed, no matter what’s happening above you. It’s hard, no doubt. But it’s also one of the most powerful leadership skills you can develop.

Your boss might be the roadblock. But you’re the one building the detour.

Over to You: What are your tips for managing upwards? Drop a comment - I’d love to hear how you’ve navigated it (or where you’re stuck).

Peace,

H

P.S. Whenever you're ready, here's how I can help you:

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