How to offer challenges to your teammates

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Think about when a manager’s helped skyrocket your growth—what did they do? Did they teach you a new skill? Did they give you hard feedback?

9 times out of 10, when I ask this question to groups of workshop attendees, people describe a time when a manager sponsored them for a visible (and often scary) stretch assignment. An assignment that these workshop participants didn’t exactly know how to do, and it felt fairly high stakes—but their manager trusted they could do it, for some reason. :) This trust, and this stretchy project, helped them grow exponentially.

In this newsletter, I’m eager to help you figure out how to offer the right kind of challenge, and to make sure that the person you’re working with opts-in to it in a healthy way (or feels comfortable saying “no” if the challenge doesn’t work for them!). Because challenges are key to our teammates’s growth. And it’s our responsibility to create them.

—Lara

Why people like challenges

I get to see folks’ initial resistance, then EXCITEMENT, about being challenged, with some routine.

For a few exercises in my full-day management workshop, participants are only allowed to offer genuinely open questions as they work with someone who’s wrestling with a problem. They’re not allowed to offer leading questions, closed questions, or give any advice. In the group debrief afterward, I ask everyone how that felt: “REALLY HARD!” is usually the first chorus I hear.

I collect feedback forms from participants after every workshop, and the majority of positive feedback I receive is about the power of that challenging exercise. Consistently. For years now!

So why do people like that super-challenging exercise so much?

Two of people’s six core needs are at work are having a sense of improvement and progress in the things that matter to them, and having the right amount of choice in their work.

Challenging assignments can help address both of these core needs. Your teammates will have an opportunity to grow and develop, AND they’ll have a bunch of autonomy as they make that progress (so long as you set up the challenge right!).

And when you offer a challenge to one of your teammates—with the explicit goal of helping them grow and learn—you get an added benefit: your teammate will feel like you believe in them, and that you trust them to tackle this challenge head on. This does more than your words about how much you trust them could ever do. (Though I believe it’s still important to say it!)

So how do we appropriately develop and assign challenges to our teammates?

The importance of Yes / No / Counter-Offer

First up: do you know how your teammate is hoping to grow?

What skills are they looking to hone? What experiences are they hoping to gather? What goals are they hoping to achieve?

The right kind of challenge is one that’s aligned with your team or company’s goals, and the way(s) in which your teammate wants to grow. Of course, there will be times when it’s much harder to find a challenge that does both—so it’ll be on you to help your teammate see why this challenge is important for them to take on. Sometimes, it’s enough to say, “I could really use your help on this right now, and though it might not seem directly related to your goals, I think it’ll help you level up on a bunch of leadership skills that’ll be valuable to you in the future.”

(This should go without saying, but: please be sure to mean it.)

Second: recognize that your teammate might just not have the capacity at the moment. Look for signs of burnout. Also recognize that external factors might be affecting someone’s ability to do work or take on a stretch challenge right now. Please be responsible as a leader, and take some care in your approach to offering challenges to your teammates.

My favorite way to make sure that an offered challenge is appropriate and opt-in is a tool I learned in coach training: the Yes / No / Counter-offer.

Before I offer a challenge, I say: “Okay cool, so I’d like to offer you a stretch goal/stretch assignment/challenge here, to help you grow. As with any challenge I offer, you can always say: yes, no, or give me a counter offer. Cool?” They chuckle, and then I share the challenge.

(When I say “challenge”, I don’t mean “homework.” Homework is, of course, a good way to make sure someone continues on their trajectory after our conversation; homework is there to help the person I’m talking to grow, develop, or just move forward on their chosen topic. But a challenge is homework that feels like a stretch.)

You can sense that you’ve offered a challenge (instead of some homework) when the person responds with, “OHHH. Wow. I… think I can do that.” Sometimes their body language changes as they sit back and need to think about whether or not they can really do that thing. That’s what we’re looking for here.

If they say “yes” to your challenge right away, but you didn’t see that lightbulb moment on their face, triple-check that this was the right difficulty setting! I usually ask, “Does that feel like it’ll be a stretch for you?” Trust their answer. If they say “not really,” ask them what (if anything) would help turn it into a stretch.

If they decline the challenge, it’s okay to ask them why! Again, trust their answer.

And if they give you a counter-offer, that’s great. Maybe they’ll stretch themselves further, or maybe they’ll need more time. However it goes, again, trust their answer.

When you come to an agreed-upon challenging project, it’s time for the final step: being explicit about the ways in which you’ll support them with this challenge.

Your continued support

“It’s not a career opportunity if you don’t get what (support, training, resources) you need to succeed.” —Cate Huston

Your teammate probably will need help with this stretch project! Maybe they’ll need some gut checks from you, or to take a course to learn this skill, or access to other people whom they can lean on as they complete the project. Go ahead and ask them: “What do you need to be successful with this?”

Support also includes telling them in what medium and cadence you anticipate they’ll need to lean on you, and for what kinds of things. Some examples:

And last but not least, re-emphasize that you know this is a stretch project for them, which means it’s supposed to feel hard. So it’s okay if it feels a bit intimidating or challenging as they work on it. Say: you believe in them, and you’re excited to support them through it.

Lara Hogan

Author, public speaker, and coach for managers and leaders across the tech industry.