Poke The Bear (But Pick The Room)

Source: Reworked, Erica McBride
Photo: ChatGPT

From promotion decisions to executive coaching, asking uncomfortable questions is how HR earns its seat at the table.

I’m someone who leans into discomfort. Not quite like my husband, an alpine climber who thinks 30 degrees below zero is the perfect temperature. But at work, with my space heater quietly humming in the background, I love pushing boundaries and asking the questions that other people avoid.

If there’s a question that everyone is afraid to ask, why does that fear exist? Why are people hesitant to send a particular email, or worried about the reaction to a report? These are often signals that something important is underneath the surface.

When I wrote about strengthening the relationship between HR and IT, I explained that part of HR’s job is to facilitate tough conversations, which means understanding and addressing discomfort. It’s easy to tag everyone in a Microsoft Teams message and cross your fingers that the discomfort goes away. But when the average employee gets more than 150 Teams messages each workday, that’s not always the best place for nuanced conversations.

When you hear “don’t poke the bear,” you might think of it as a warning not to stir up unneeded trouble. But I see it differently, because in HR the problems are usually already there. Poking the bear is how you find out how big the issue is while you still have time to do something about it. And as work speeds up (especially with AI), slowing down at the right times matters more and more.

Ask ‘Why?’ – and Keep Asking

You’re probably familiar with the five whys — asking “why?” five times to get to the root cause of an issue. It’s a smart approach, but so many people don’t even ask one “why?” because they’re afraid it could be interpreted as an attack, even if it’s just a fundamental question about a business decision.

A lot of my job involves holding up mirrors for people, so they can see their decisions reflected back as questions to take a more objective look as they consider their intentions and actions.

For example, if an executive wants to promote someone on their team but the employee doesn’t meet the traditional criteria, I’m going to ask why this employee, and why now. Maybe I’m not seeing something that the supervisor sees, and I need them to help me understand how they reached their conclusion. Best case, the leader gives their rationale, it makes sense and we move on. But if the decision isn’t justified, asking “why” can quickly show you where the foundation isn’t holding up.

Ask ‘What Happens If …’

My job isn’t necessarily to teach someone, but to hold space, walk through the different scenarios and reassure people that they’re not going to take a professional hit just because they have some doubt. We need to ask: What happens next? Is this decision a lead domino? What are the different possible trajectories?

Sometimes we realize that a five-alarm fire on a Monday morning will probably put itself out in a day. Other times, it’s worth running a pre-mortem to imagine a failed project, then work backward to figure out how to make better choices today.

At a time when work is speeding up, these calculated pauses are crucial. Microsoft research shows that the most advanced AI users are much more likely (53% vs. 33%) to say they “intentionally pause before starting work to decide what should be done by AI versus a human.” If the most advanced employees take an extra beat, maybe the rest of us should, too.

Executive Coaching Is Poking the Bear

A CEO survey found that 72% of CEOs experience loneliness — but only 12% have a formal CEO coach. That’s not surprising. But as an HR director, it’s disappointing anytime I hear that leaders are making difficult calls without the support they may need.

Leaders are typically moving quickly all day, every day. They have 900 things in their head competing for the same space. That’s why HR needs opportunities — even if it’s just an hour each quarter — to ask questions and let leaders talk. One of the magic moments for me is when an exec says, “I don’t know, I just have a feeling about this.” Maybe there’s something else competing for their attention. Or maybe we need to keep asking questions until we unlock what’s really going on.

As someone who’s helped develop talent at Apple and other top companies, I’ve seen that leaders often express initial hesitation about executive coaching. But even the most resistant leaders are usually talking through these decisions with someone when they go home at the end of the day. Unfortunately, these partners don’t have the organizational context that HR does. We know the players. We know the playbook. And we know exactly where to poke to help these leaders succeed within the organization.

Poke Within a Safe Environment

We recently finished a cycle of quarterly meetings where we asked a lot of “why?” questions: Why did we do that? Why does this keep happening? Why are we moving this person now?

What made these meetings especially effective is that they took place in a closed room with senior leaders who were prepared to be questioned. You’re still poking the bear — but now you’re dealing with teddy bears rather than grizzlies.

It’s important to give leaders a space where they can be vulnerable without consequences or people questioning their ability to lead. A survey earlier this year found that 63% of senior leaders said they’d ask for input on big decisions more often if they didn’t think it would make them look weak. As I’ve written about previously, creating a safe environment gets easier when you build a high-trust organization.

Why HR Needs to Be Part of the Conversation

A recent report from Kyndryl found that workforce readiness is the “ROI difference maker” in AI adoption. People matter as much as the technology in many implementations. Yet 46% of organizations don’t include the head of HR in defining their AI strategy, according to IBM. Now that’s a bear that deserves a giant poke or two.

Whether you’re in HR or any role that’s not always the loudest voice, you can still be the one who asks the uncomfortable questions. Just pick the time and space carefully, and make it safe for anyone to answer with, “I don’t know … but let’s talk about it.”

https://www.reworked.co/talent-management/poke-the-bear-but-pick-the-room