Stay Connected to Your Remote Team With These 7 Questions

Powerful, relationship-enhancing inquiry keeps your finger on the pulse


Shane Kinkennon

3 years ago | 4 min read

For supervisors whose approach to management is connectedness and high rapport, remote work has thrown a painful curveball.

This fact was highlighted for me in a conversation earlier this week with my friend and former colleague Steve Behm, a regional president at a global public relations agency.

Steve explained that traditionally, he’s watched his team closely for signs of anxiety, stress or overwhelm — body language indicators such as rubbing one’s temples or being curt with coworkers.

When a staffer appears to be struggling, he finds a private moment to offer a heartfelt check in, and if he can has a coaching conversation to help them work through their challenges.

It’s a method he’s come to rely on to ensure engagement by his team and top performance in client work while simultaneously maintaining a sense of respect and humanity in what can be a high-burnout field.

Of course, Steve’s method was a great deal easier at the office because of the open floor plan surrounding where he sits.

He could literally see his people all day. Now that everyone is at home, Steve holds regular video check-ins with each of his staffers, asking the kinds of questions that have proven effective for him in the past, watching for body language where he can.

But as we’ve all learned, it’s not quite the same. He’s concerned that a member of his team might struggle in silence, experience attention drift, or become detached. It’s far more difficult to see when a helping hand or supportive gesture is needed.

Stressful transition for those who lead from the heart

I’ve found that the transition to remote work is particularly challenging for managers and supervisors who have high emotional intelligence, those leaders who ensure performance by being highly in tune to morale, mood and spirit. They are left relying on Zoom conversations.

The key, then, is to make those Zoom conversations as high quality as they can be. That means skipping default questions like “How are you doing?”

Such questions tend to elicit little more than “I’m fine.” Thankfully, there are alternatives — really powerful questions that faciliate the kinds of frank, open dialogue that keeps authentic connectedness in place.

Here are seven of my favorite powerful questions that will get your folks revealing more of what matters most and help you keep your finger on the pulse.

1. What’s something you did well this week that you probably won’t say out loud if you don’t right now? This questions prompts your team member to pause and reflect on a small win, something as simple as taking a tough piece of feedback in stride.

You’ll spark them to see what is achieved and even indulge in a sense of accomplishment. And you’ll show that you care enough to be there for it.

Pro tip: Add “How will you celebrate that? Your team member will feel great hearing you insist, in a way, that they pause and take stock when good work has been done.

2. Where are you feeling incomplete? With this question, you can nudge your team member’s focus from task orientation to thinking in terms of whole accomplishment.

It’s terrific for drawing out little personal victories or, conversely, what may be nagging at them. They’ll see that you care about their sense of fulfillment, a great investment in relationship. (This terrific question I learned from my executive coaching mentor Andrew Nietlich.)

3. What would you like to see happen next? With this question, you remind your team member that their input is valued and that they have agency. It also subtly shares accountability for creative problem-solving. (This question was suggested by Dennis Sanchez, a professional health-and-wellness coaching expert who trains other health coaches, and who also happens to be my spouse.)

4. Pick something that really matters to you and tell me what’s standing in the way. With this question, you’ll challenge your team member — or maybe better stated, give them freedom to — ponder both external and internal inhibitors to progress. It’s a powerful question for drawing out insight while underscoring that you’re in their corner.

5. What’s one thing you might do that would make the biggest difference on something you’re working on? With this question, you’ll remind your team member of their considerable capacity to be their own best solution crafter.

By inviting them to focus in on one high-impact move, you play the role catalyst for getting themselves unstuck and moving again. They’ll be grateful to you for it.

6. What means the most to you personally about something you’re working on right now? This question is great for showing a team member who is wrestling with a tough topic that you care about their intrinsic motivations.

It shows that you’re concerned only with output and results but with what makes them tick beyond the paycheck. (I give Govert van Sandwijk credit for this one, which is in the list he shares in this post.)

7. Tell me about something that has you feeling optimistic. This question is a great closer when your team member is preoccupied with what’s difficult. It reminds them to focus on what’s doable and what inspires them, and positions you as the person who gives them latitude to do so.

Pro tip: Try creating casual-conversation moments to pose these questions rather than leaving them to more formal one-on-one meetings.

For instance, try a Friday afternoon unannounced phone call. Say, “Hey, I don’t want status reports on anything. I just thought I’d pause, check in, and see how you’re really doing.” Pose a few of the above questions and see what happens.

I’m not suggesting it’s in any way as easy to lead with soft skills while working remotely as it is while working in person.

But if you raise the quality of the questions you ask, shake up when you ask them, and listen deeply for meaning in the responses you receive, you’ll come closer to the the high level of connectedness you’re accustomed to.


Created by

Shane Kinkennon

Certified Executive Coach. I work with CEOs of company up to $500M to help them get the most of their human capital and to lead change.







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