Issue 104 October 7th, 2026 | | |
Before we get to our featured topic, I just wanted to thank everyone for their birthday wishes last week (it was one of those “ends in 0” birthdays) and for pre-ordering Be the Boss You Wish You’d Had. If you did order the book, please start taking advantage of early access to our companion toolkit available here. Daniela and I are also going to be doing a weekly series covering key topics from the book for those who pre-order – yet another reason to buy early.
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On the topic of management, one thing I’ve learned over the years – sometimes the hard way – is how important it is to have a good working relationship with your boss. Managing up well doesn’t mean you need to be BFFs. It doesn’t mean you need to agree all the time. It shouldn’t mean that you play politics, or that you focus on your boss at the expense of your peers or others. But learning how to manage up well – in general terms and in ways that are specific to your boss – is something most of us should focus more on.
Why?
Because your boss has an outsized influence on your working life. They shape what you work on, how much autonomy you have, what development opportunities you’re offered, the visibility you get, your compensation and promotion prospects – and ultimately whether you enjoy coming to work every day.
Many people assume that because the boss is in charge, it’s their responsibility to make the relationship work. And that’s...well...just wrong. You also bear that responsibility – and it’s in your interest to take that on. Hence the accompanying image of riding a tandem bike together.
Hopefully you get the importance by now, but what does effective managing up look like? Here are seven practical tips:
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Learn your boss’s operating system. Some bosses want detail, while others want only a quick summary. Some want to be consulted before decisions are made, and others expect you to act independently. So figure out how your boss processes information, makes decisions, and wants to communicate. And if you’re unsure, ask.
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Understand their priorities. Your to-do list connects to only a part of your boss’s to-do list. Learn what they’re trying to accomplish, what pressures they’re facing, and what they’re worried about. That context will make you more effective.
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Make their job easier. The best employees reduce their manager’s burden. They keep drama to a minimum, work well with their colleagues, follow through on commitments, anticipate questions, and bring potential solutions rather than simply flagging problems.
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Communicate deliberately. Agree on how often you’ll check in, what warrants an immediate conversation, and what decisions you can make yourself. Above all, avoid surprises. Unlike wine, bad news rarely improves with age.
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Build trust through reliability. Do what you say you’ll do. If you’re struggling, ask for help. If something will be late, say so before it’s too late to do something about it. If you make a mistake, own it. You want your boss thinking, “If they say they’ve got it, they’ve got it.”
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Learn to disagree well. Managing up doesn’t mean agreeing with everything. Bring evidence, ask questions, offer alternatives, and challenge constructively. Importantly, though, disagree before the decision is made. Once it has been, get behind it and commit to making it work.
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Ask for what you need. Don’t assume your boss is a mind-reader. If you want more feedback, responsibility, exposure, or a promotion, bring it up. And when you ask, be specific. Let them know how exactly you’d like them to help you.
Managing up is ultimately about working effectively with someone who has significant influence over your career. You can’t control how your boss manages you, but you can definitely take responsibility for your half of the relationship.
JR and the PathWise team
| | October 5 – Podcast: Success Isn’t Enough: Building a Work Life Worth Living, with Jeff Westphal. What does it take to build a career – and a life – with real intention? Jeff Westphal shares how a serendipitous discussion led to a life-changing epiphany that fundamentally changed his approach to leading his firm, Vertex, through tremendous growth over two decades. It’s a thoughtful discussion about purpose, relationships, and success on your own terms. Available here. | October 5 – Resources: Decision Fatigue. Researchers estimate that the average adult makes 35,000 decisions each day. Though many of them occur on auto-pilot, the remaining ones often involve more choices than we’ve had in the past. All that choosing can easily become exhausting and contribute to decision fatigue. We’ll talk about ways to reduce the decision burden you face each day with practical tips and tricks. Posts available on LinkedIn and in the A to Z Guide in the PathWise Member Community. | October 6 – Office Hours: Authenticity. What does it really mean to be authentic at work, and how do you stay true to yourself while adapting to different people, roles, and situations? In this session, we'll explore practical ways to lead and work authentically, build trust, navigate expectations, and find the right balance between authenticity and adaptability - and being your true self and over-sharing. Check out the replay | October 12 – Podcast: Stop Following Someone Else’s Career Playbook, with Andy Paul. Are you building the career you want – or following someone else’s playbook? In this episode of Career Sessions, Andy Paul shares his thoughts on when conventional career advice can lead us astray, how to make more intentional choices, and why defining success for yourself may be the most important career move you make. Available here. | October 12 – Resources: Delegation. Many managers struggle to delegate, either because they’re worried their team won’t do a good enough job or they struggle to let go of the work themselves. But delegating well both frees you up to focus on more important tasks and builds capabilities in your team, making them more independent. We’ll share our thoughts and others’ perspectives on how you can learn to delegate better. Posts available on LinkedIn and in the A to Z Guide in the PathWise Member Community. | October 13 – Office Hours: Project Management. You don't need to have "project manager" in your job title for project management skills to be important. Almost every task you complete at work is a "project" of sorts, and success is about getting the right things done, with the right people, at the right time. Join us for practical guidance on setting priorities, building realistic plans, managing stakeholders, staying ahead of risks, and keeping projects moving when things don’t go as expected. Register today! | October 19 – Podcast: You’re Always in the Job Market: How to Manage Your Career Before You Need To, with Kelly Kay. A lot of people spend plenty of time focusing on how to succeed in their jobs but far less time thinking about how to choose the right jobs in the first place. Kelly, a managing partner at executive search firm Heidrick & Struggles, shares an insider’s perspective on how to manage your career more deliberately. The discussion offers plenty of advice for active job seekers and the rest of us.Available here. | October 19 – Resources: Deliberate Practice. As professional athletes know, there’s practice and there’s deliberate practice. Practice means putting in the time, sometimes more than is really needed, under the belief that more is better. Deliberate practice adds the notion of working on specific skills in each session, and that sharper focus often translates into higher performance with less time practicing. This approach can benefit not just pro athletes but you as well. Posts available on LinkedIn and in the A to Z Guide in the PathWise Member Community. | October 20 – Office Hours: Candor. Candor is essential to strong relationships and high-performing teams, but being honest doesn’t mean being harsh. Join us to explore how to communicate openly, give and receive difficult feedback, address issues before they grow, and create an environment where people can speak honestly while maintaining trust, respect, and strong working relationships. Register here. | Do you want to be the boss you wish you’d had (or maybe even the one wish you had now)? Of course you do!! So check out J.R. and Daniela’s forthcoming book, available for pre-order on Amazon, Barnes & Noble, and through other book retailers. | If you haven’t signed up yet for our member community, do it today! You can keep your free membership or upgrade to one of our paid member tiers. Sign up here. | | |
Know others who need career support – and don’t we all? Send them this newsletter and encourage them to check us out!
And please give us your feedback, on this newsletter and PathWise more generally! You can drop a suggestion in the Suggestion Box in the new member community or email us at info@pathwise.io.
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