3 Important Conversations to Have With Your Boss

Great bosses, lousy leaders and every type in between, we all have a Big Cheese in our lives.

But no matter if your manager is the epitome of approachable or the reason the phrase “keep your head down” exists, there are conversations you should take the opportunity to initiate. For some of you, that will be easier said than done. Others will read this and think, Dude, I’ve got this. It depends on personality (yours and your leader’s) and the tenor of the relationship you share.

As a founder and CEO, I appreciate candor from Reputation.com employees. It doesn’t mean I’ll necessarily agree with everyone’s viewpoint every time, though I often do. But it does mean that hearing additional input and new perspectives gives me a chance to consider something important through a different lens.

Here are three conversations employees have taken the opportunity to have with me:

“Here’s What I Need From You.” Some leaders think that personal feedback is a one-way street – they deliver it straight to employees and boom, that’s it. In fact, it should be a two-lane highway: employees need to give it back to leaders too. Bosses have bad days like everyone else – we have fights with our spouses, a child we’re worried about, a sick parent. We don’t always have the introspection to see how we’re coming across to everyone at every moment – or how deeply these interactions affect the people who work for us (though most of us typically try valiantly). Phrase it nicely by couching it in the impact to the business: “It would help me meet our production deadline if I could get your feedback more quickly. Should I set up an in-person to discuss next time?” Trust me – we’ll hear what you’re really saying: “You took three weeks to get back to me despite every attempt I made to remind you this was urgent.”

“Have You Considered This Wrinkle?” I don’t know you but I don’t have to: you have perspective your boss does not. Period. That’s not to say your boss doesn’t have a good idea of what’s going on – but the nuances are yours, delegated to you to by virtue of your position. It’s up to you to give your manager the fullest picture possible by ensuring she has the relevant detail. Take note: that’s not every tiny detail, only the pertinent ones. If your lead is preparing to go to her boss with a new initiative, and you just heard about a delay from your engineering counterpart, speak up so she can recalibrate with the most current intel. Leader bounces an idea off you? Feel free to say “Have you considered XYZ potential impact?”

“I Have to Try Something New and Different.” Employees typically dread this discussion but good leaders know that high-performing employees need new challenges to stay fresh and engaged. Rest assured: it’s not the first – nor will it be the last – time we’ll hear from someone who likes the organization and people, but just doesn’t feel energized anymore. Come prepared with ideas on what you would like to take on. Are there stretch assignments that meet a business need while giving you an opportunity to learn something new? Want to make a jump to a completely different department and job? Show us how your skills and experience would translate. Leaving altogether? That's also a natural part of professional progression.

What conversations have you successfully initiated?