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Jane, head of engineering for a startup business within a large corporation, was talking with Adam, head of engineering for a different group in the company.

“I get so overwhelmed with all the negative I face every day,” Jane declared. “We are making progress, faster than I ever expected. Our people are engaged, happy, and building the future. And yet, it’s never fast enough or close enough to my stakeholders’ vision. My people feel frustrated because they never hear ‘Good job’ from anyone outside our team. The teams we need to work with appear terrified we’re putting them out of business. I’m so—” Jane blew out a frustrated breath and slumped in her chair.

“I feel for you,” Adam replied. “Building the future is hard enough when everyone agrees on what it looks like and whether to even do it. When everyone seems out to get you…that’s tough.”

Jane nodded despondently. “You’ve been through this a number of times. How did you survive?”

“I ask three questions of three sets of people.”

Invite their self into the conversation

“The hard part for me has always been knowing the people browbeating me are, in fact, happy with what I’m accomplishing,” Adam began. “They’re being pushed by their stakeholders, who are being pushed by their stakeholders, and so on.”

“That feels accurate.”

“So, I get them to acknowledge what’s going well.”

“How do you manage that?”

“As you say, they’re hyper-focused on everything that isn’t going well. I tried borrowing from the standard retrospective questions and asking, ‘What’s going well?’ ‘Nothing,’ is all I ever heard. So, I tried some variations. What I discovered works consistently is, ‘What do you like?’”

“’What do you like?’ How does that phrasing make any difference?”

“No idea. Well, maybe it lets them bring themselves into the conversation, where ‘What’s going well?’ invokes everyone pressuring them. Some people laugh and say, ‘Coffee’ or ‘Racquetball’ or something completely off-topic like that. Then, they get into what they like about the project.”

Jane nodded thoughtfully. “Makes sense. You’re explicitly putting the focus on them. That helps them feel seen, I bet.”

“Could be. I hadn’t thought of that angle. It’s like I’m instantiating them, rather than letting them present as a proxy for the people on their case.”

Ask them to dream a little

“So, ‘What do you like?’ is your first question. What’s the second?”

“’What do you wish?’”

“You’re rewording the standard retro ‘What’s not going well’ or ‘What could be going better’ question.”

“Yep. And, again, I don’t know why it works. Probably all the same reasons rewording the first question does.”

“And so your third question rephrases the ‘Action items’ or ‘What should we do about it’ question?”

“Indeed. ‘What do you wonder?’”

“I like it. You’re asking them to dream a little bit. Go beyond what is known or expected and exercise their imagination.”

“Yes. Although, I didn’t know that until you said it just now. Thank you for helping me understand why these questions work.”

Start with yourself

“So, that’s the three questions you ask. Who are the three sets of people you ask these of?”

“The first is me. I need to bring myself into the conversation and understand where I am.”

“Smart. I often neglect to do that.”

“It’s not something we’re taught to do. And, when we have grumpy people breathing down our neck, it can be challenging to take the time.”

“If you start by asking these questions to yourself, I’m going to imagine you next ask them of your team? And then of your stakeholders?”

“Yes and yes.”

“What’s special about that? I always try to involve my team. And my stakeholders are already making their opinions known.”

“I agree this is straight out of Management 101. I noticed, however, that I often neglected to check in with my team. As for my stakeholders, I wanted to deflect their aggression and redirect it into channels useful to me.”

“When you put it like that, I feel rueful. It seems so obvious when you say it. But, you’re right: I forget to ask my team what’s going on with them, what they want to do. And deflecting my stakeholders’ aggression would be a big help.”

“Just because something is obvious doesn’t mean it’s easy. Nor that we remember to do it.”

Leading others starts with leading yourself

“This is maybe the most information-dense help-providing conversation I’ve ever had. Helping my browbeaters feel seen, inviting them into the conversation, can help them shrug off their own browbeaters and be willing to be vulnerable and offer their own opinions. Even more impactful is asking them to engage their imagination. This can work with my stakeholders. It can also work with my team. And, most importantly, with myself.”

“Excellent summary and paraphrase. That last bit is the most important.”

“’Most importantly, do these with myself?’”

Adam nodded. “Most importantly, do these with ourselves. Leading others has to start with leading ourselves.”

Jane goggled at Adam. “Adam, you’ve managed to pack even more information and help into an already stuffed conversation. Thank you.”

Adam chuckled. “You’re welcome. And, the expression on your face just now was priceless. Thank you.”

Jane doffed an imaginary hat and said, “You are most welcome, sir.”

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