Modern Mentor

4 questions to ask yourself when someone has disappointed you

Episode Summary

One theme that’s been coming up a lot lately is disappointment.

Episode Notes

Disappointment is a part of life. True. But sometimes there’s real intelligence in disappointment. When we feel disappointed by others, our instinct is typically to blame. But sometimes getting curious about what caused a disappointment can help us prevent them in the future.

Modern Mentor is hosted by Rachel Cooke. A transcript is available at Simplecast.

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Episode Transcription

Hey, it’s Rachel Cooke, your Modern Mentor. I’m the founder of Lead Above Noise—a firm specializing in helping teams and organizations optimize their working experience. Right now I’m spending a lot of my time running cohorts of new leaders through my SIMPLE group coaching program. One of my favorite things about this program is how much insight it gives me into what’s really top of mind for new leaders. Which helps me keep our conversations relevant.

One theme that’s been coming up a lot lately is disappointment. Like, leaders seeing team members continuously drop the ball. Or leaders giving team members a shot to do a thing, and the thing belly flops. Or leaders giving feedback to team members whose behaviors just aren’t changing. All of these situations—and many more—can trigger real feelings of frustration and disappointment. And leaders, naturally, are looking for guidance on how to turn things around.

While they’re often looking to me for help on “fixing” their teams, my advice—which they often hate until they give it a try—is to do a bit of reflecting on what may be going on here. Because so often when leaders (yep—me included) are disappointed by someone else, the truth is the leader played a role in that not-so-hot outcome.

And our job is to figure out what went wrong so we can change the outcome next time.

Here are some questions I urge leaders to think about when team members do a thing that needs to be undone or redone.

1. Were my expectations clear? 

Last week, after peeking into my teen daughter’s room and seeing a 5-alarm disaster scene, I told her she needed to clean it up. Like, now. And I’d hold her phone for collateral until it was done.

An hour later, sweaty but proud, she came downstairs to declare victory.

After a quick peek at a room whose floor I could actually see, I returned the phone. Later that day I went to grab something from her closet, and…well…you can only imagine the avalanche.

I was mad. I felt like I’d been duped. But when I confronted my kiddo, it was clear that wasn’t her intent. She’d seen me react to the state of her floor. And so assumed that by “clean your room” I’d meant “make things not be on the floor.”

Now you can make any assumptions you’d like about my parenting. But I’m giving her the benefit of the doubt here. “Clean” is a really subjective word. Especially when one of the interpreters of it is only 13.

This same dynamic plays out in the workplace all the time. A leader tells an employee to write up a report or create a presentation or develop a pitch or build a model. But without specifics around length or quality or completeness or content… it’s so easy for the leader to imagine one outcome and the employee to assume another.

So next time you’ve asked for thing A and received a disappointing thing F, start by asking yourself—were you crystal clear in what you asked for? And how can you refine your ask next time to ensure greater alignment at the start?

2. Were my expectations reasonable for this person? 

Because being clear about the outcome is one thing. Being sure this person is able to deliver that outcome is another. And that answer is so specific to the person.

In my situation you might be thinking—of course a 13-year-old is capable of cleaning her room! For some, that’s absolutely true. But mine has some neurodiversity stuff going on, and in hindsight, it was a really big and daunting task for her.

My kid needs smaller chunks—like “put away 4 shirts” or “throw out any garbage” to help her process and organize.

At work, your team member may not have access to all the tools or data they need. Or they may be missing some context you haven’t shared. Or they may be new to the company and don’t know your norms or language yet. Or they may be super creative and you’ve assigned them a highly analytical project. Did you provide a reasonable timeline?

“Reasonable” is relative. And part of being a leader is knowing your people and their strengths and limits, and leaning into them accordingly.

3. Did I offer the right support? 

Clear expectations plus the right person is a recipe for success. But even when you get those right, things can still go off the rails at any time.

Along the way we hit roadblocks, we have questions, we need permission or air cover or support. And sometimes we just need to check in and confirm we’re on the right path. And course-correcting while something is still only 20% baked is so much easier than getting to the finish line and learning the whole thing is just wrong.

Really reflecting on how available you were, how open to questions, how responsive to requests, how willing you were to coach and offer feedback along the way… all of these played a role in whatever the outcome was. So consider for next time where you might have room to be more present and supportive along the way—rather than being the judge waiting at the finish line.

4. Did I articulate a clear “why”? 

Sometimes we can get all the things right. Right person, well supported, with clear expectations. But still. The end result just falls… flat.

And this can happen for many reasons, but most commonly when we’ve neglected to help them understand the outcome’s purpose. Why this thing really matters, and to whom.

A friend was recently asked to put together a presentation of the work his team had done in recent months. Assuming this was going to be presented to executive leadership, he was sure to use lots of lingo, and pulled in plenty of data and detail designed to impress!

Turns out, his boss actually needed the presentation for a recruiting event he was planning to attend. Which means all of it—the tone, the level of detail—was wrong. And he had to start again.

When we understand the purpose of something we’re being asked to do, we can use our judgment to make the right choices—choices that will serve the quality of the outcome.

So next time you’re feeling down on your team for something they’ve missed the mark on, give some thought to how you might have played a role in the miss. And what can you do differently next time?

Join me next week for another great episode. Until then, visit my website at leadabovenoise.com if your organization is looking to dial up its Employee Experience or deliver some leadership development that activates change. You can follow Modern Mentor on Apple Podcasts, Spotify, or wherever you listen to podcasts. Find and follow me on LinkedIn. Thanks so much for listening and have a successful week.