Q&A: Helping Struggling Colleagues (and Yourself)




For this week’s Sensemaker, we’re doing a new format—the Q&A!


“What do I do if I think I notice a leader struggling a bit? I don’t know how to raise it and don’t want to offend anyone, but I do want to be helpful if I can.”

First, this is a great question, and I was excited to see it come up. It’s all too easy to forget that our leaders/managers are people, not just roles. They have good days and bad days. They have their own stresses, on top of which they’re often carrying a great deal of responsibility for the success of the firm and their people. Many leaders believe leadership requires always showing a strong face so the people who report to them don’t worry, making it a lonely position without many easy avenues for getting support.

Here are a few tips for supporting your leaders and managers:

  1. Share your desire to help: Often, leaders may not even realize you’re available for more on top of what you’re already doing. Let them know that you want to pitch in to help the team succeed, and ask if there are any particular goals they’re working toward where they could use some leverage. Then, make sure you follow through so that leaders feel they can actually rely on the help that gets offered.

  2. Do the sensemaking work for them: One of the hardest (and least-seen) burdens of leadership and management is having to continually put everyone’s work into the bigger picture, and help people make sense of what they’re doing. Now is the time to do everything you can to make your existing output easy to parse. Set context up front in every conversation, starting with your understanding of the goal you’re trying to achieve, and be clear on where you stand against it. Put extra effort into summarizing and formatting work, such that the information most pertinent to any decisions they have to make is easy to see. When you review work together, note what they focus on, and make sure that’s clearly accessible in any other work going forward.

  3. Proactively share information: Another invisible burden of leadership is having to continually put in effort to understand what’s going on across the team. This is both one of the first things to drop when a leader is underwater, and a big source of ongoing stress the further it gets away from them. You can help by going the extra mile to gather data on how everything is going around you—across deals, across teams, etc.—and proactively sharing it with the leader (having put in the extra legwork to synthesize it, of course, per the point above).

“What do we do if one of our colleagues (or team members) seems to be struggling? They are grumbling more than usual, pessimistic, etc.”

At a principle level, anytime someone’s behavior (or a given circumstance) is provoking a reaction in you, the place to start is always with you. What is bothering you about the behavior that has you wanting to go into action? Is the negativity tapping into angst you have yourself that you’d prefer not to look at? Do you have a judgment that the “grumbling” is a distraction from what you’re trying to get done? Whenever people behave differently from what we expect, it creates confusion, and the first step to dealing with any kind of confusion is to bring it into our active awareness so that we don’t take knee-jerk action that often ends up making things worse. “Starting with you” you can achieve two goals with one move: increase the probability that you will learn about yourself, and be in a better position to help the other person. Starting with the other person reduces the chance of both.

Once you’re clear on where you’re coming from, you can move to how things should work, meaning the roles, goals, and processes at hand. ​If this is a direct report or someone you’re otherwise counting on for some kind of output, then start with that reality. No one wants to be manipulated. “Hey, I’m focused right now on achieving X, and I can’t do it without you. I’ve noticed you seem to be having a rough time these days, and if you think it’s going to have an impact on our ability to get X done together, I want to get out ahead of it. This isn’t about making you wrong—it’s making sure we’re on the same page that X is important, and that I know if there are risks to that.”

Then, regardless of the roles/goals, it’s worth recognizing that the person behaving in a way that concerns you is likely deeply confused/in some kind of threat. The meta-goal here, regardless of the relationship, is helping them get clarity.

Most people want to be helpful. This translates into most of us also having triggers around not being helpful, feeling stuck with someone, feeling like we have no influence, etc. The net impact is that most of us jump straight in with solutions or offers to help without actively exploring the underlying confusion.

​The problem with this approach is that it doesn’t address the root cause of the issue, doesn’t actually help either of you learn, and sets the stage for more confusion for YOU when the intervention doesn’t yield the outcomes you wanted.

​So the next question (for you) after roles/goals, is whether you genuinely have the bandwidth to go into an open-ended exploration with the person. If not, then just stick with “hey, noticed you seem to be having a hard time, let’s find time to connect later,” and reach out when you do have that bandwidth.

​Once you do, it’s time to put on your investigator hat and remind yourself that the goal is understanding, not fixing or comforting (which tend to be counterproductive in a work context).

​Then jump in! You can start with the observation: hey, noticed you seem to be having a hard time, etc. Then get consent: I’d love to support you in this, are you open to that?

Once you have that, follow your curiosity. What are they experiencing? How is their experience different from what they were expecting? What emotions do they have around that gap—fear? Anger? Sadness? Something else?

​There are levels of mastery to how you do this, but the key principle is that if you help the person get clear about what doesn’t make sense to them and what’s painful about that, you’re well on your way to helping them. Then you can start exploring what IS meaningful to them: what do they care about, how can they pursue that in their current work, etc.

“I’m concerned about my ability to add value at the moment, and am having a hard time with the travel ban and concerns about my longer-term job security. I’ve not found a way to raise this with my superiors—it feels like being high maintenance when they have so much else on their minds.”

Before going into an answer, I want to normalize the feelings behind the question. I’ve been privileged to hear the inner worlds of some of the highest achievers in the world, and I can tell you that doubt, fear, impostor syndrome, uncertainty about how to add value or get clarity are all extremely common, even (perhaps especially) amongst people driven to succeed.

It’s not surprising to me that these feelings would arise in a dislocation like what we’re experiencing now. It’s a double whammy—we’ve all lost many of our everyday touchpoints (like being in the office) on top of macro uncertainty. This means that our brains are trying to make sense of a new, uncertain context, without the typical signals that help us make sense of it. When we can’t make sense of things, we’ll almost always retreat into fear narratives about ourselves and others.

For the tenor of this specific question, it sounds like a loss of clarity about vision and goals (and how your responsibilities help achieve them). And the typical way you’d resolve that confusion (go to your manager) feels inaccessible because of stories about their own overwhelming situations (maybe true, maybe not).

I’d recommend carving out 30 minutes or so for yourself to step back and reorient to the larger vision for the company, your current goals, and your current responsibilities.

What is most important to achieve right now? Do your current goals/responsibilities still map to that, or has COVID changed that picture?

If the latter is true, you will want to sync with your manager. However, do so after having done the heavy sensemaking work for them.

For that, step back and write down:

  1. The big-picture vision.

  2. Your understanding of the current most important goals for your team and the broader firm, and how they support that vision.

  3. How you understand those goals to have changed (or not) because of COVID.

Then, take a moment to look at that picture, and write down a few hypotheses for how you could change your responsibilities or try new things to help achieve those goals.

Once you’ve done this, you can go to your manager with a clear picture of how you’re holding the broader firm/company goals, how you believe they’ve changed, what that means for your responsibilities, and potential new things you’d like to try to add more value toward those goals.

Having done the sensemaking work for them, it can be a quick sync conversation (that may give them inspiration as well!) rather than a murky problem they have to drop down to fix.

  • What signs have you seen of your colleagues having a difficult time with the COVID context?

  • Have you tried to help? How? If not, why not?

  • What were the results?

  • Write down a question related to a current sensemaking struggle in your professional life.

  • Send it to info@talentism.com


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