Improving your relationship with your boss starts with being more aligned on priorities

Globe and Mail

08-05-2025

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Melody Wilding, an executive coach and professor of human behaviour at Hunter College in New York City, believes that most of the stress and frustration people experience with their bosses is fixable, because it stems not from pure incompetence or antagonism but a lack of awareness on both sides about how to work together effectively.
'Most professionals know they need to manage up but few know how to do it well,' she writes in her new book Managing Up.
The first step, she advises, is to adopt a strategic, investigative mindset. As you start to see your boss less as a gatekeeper or overseer and more like a human being dealing with their own pressures, distractions and demands from higher-ups, you will begin to discover what drives their decisions and unlock how best to communicate with them.
That may seem unbalanced. Making the relationship work better is falling upon your shoulders. But she asks you not to view it as making your boss's life easier. It's about taking control of your own work experience. 'Even if you have a good relationship with those above you, why settle for good when it could be great,' she writes. 'Consider it an investment in your satisfaction at work.'
You will need conversations with your boss to ensure better alignment, so you don't seem pulled in 100 different directions or spend so much time trying to decipher cryptic feedback or mixed messages. You want to figure out how your work fits into the bigger picture and make sure you and your boss agree on success.
'No more emotional drain from doing what you think your boss expects, only to get it wrong and face frustration and disappointment,' she says. 'You can replace any simmering tension with a sense of shared purpose and understanding.'
Beforehand, she suggests spending some time figuring out your one-year vision – what work would be like 365 days from now if it was the best possible situation. What would you be doing? Who would you be interacting with? What would make the day energizing and fulfilling? What key projects might you be leading? What organizational changes can you foresee now and how can you best prepare?
That will allow you to understand where you want to steer. Now you are ready to get into your boss's head. In upcoming one-on-one meetings and more general conversations with your boss, she recommends weaving in questions like:
If it's your first time bringing up alignment or the relationship with your manager has been rocky, she warns you will need to ensure the questions don't seem to come out of nowhere by indicating your overall desire to understand things better. And the answers won't necessarily be crystal clear. You will undoubtedly need to dig deeper with further questions.
Bringing yourself in alignment with your boss can help improve the relationship dramatically. You will want to supplement that by subsequent observation and conversations on issues like differing styles, how to get beyond bottlenecks and take greater ownership of your work, providing feedback to the boss on frustrations such as their lack of vision to favouritism to other colleagues, how to position yourself for promotion and remuneration. Managing up is part of your job.
Harvey Schachter is a Kingston-based writer specializing in management issues. He, along with Sheelagh Whittaker, former CEO of both EDS Canada and Cancom, are the authors of When Harvey Didn't Meet Sheelagh: Emails on Leadership.