Reflections on leadership: The comfort conundrum

As a follow up to my post reflection on leadership in the digital era, I wanted to dig a little deeper and explore some specific areas of leadership that sometimes go unexplored, or unsaid. Its my hunch that being explicit about behaviours that both empower or diminish you and your team might be valuable to others. Worst case, I’m just rambling on here by myself and there’s still value in that for me. In this post I want to explore how prioritizing comfort is an accidental diminisher that has a negative effect on you and those who you are in leadership with.

Comfort at a systemic scale

The past two years of reckoning that have brought the issues of indigenous reconciliation, BLM, and the systemic inequities laid bare by COVID have had a profound impact on how I think about comfort. As a privileged white person, I’ve been socialized to believe my own comfort is my right… It’s a lie. Things are mostly comfortable for me because it’s come at the expense of generations of others for whom the optimization for whiteness means systemic racism and oppression. We’re seeing how uncomfortable some have gotten as social justice movements gain ground and start chipping away at inequality and systemic barriers. At the heart of almost all opposition to change is a fear of loosing comfort. I’ve come to see that comfort is essentially the bedfellow of oppression. If you are still unsure what this means, you might have some more reading to do (we all do and that’s okay.) I’m still working on my own journey to understanding my whiteness and privilege.

Its possible that you’ve not given comfort any thought… or examined the ways in which comfort is showing up in your organization or your own leadership. If you are comfortable with how things are, you’re likely privileged within your organization in some way. Many of the organizations which we work in, are biased towards comfort. You might not be “choosing” comfort… it simply is the invisible default. It’s expected.

Or you maybe someone for whom comfort is not an option, never mind an option to disrupt the comfort of others. Expressing needs or flaws in the current status quo may put you in harms way, especially if you’re from a marginalized or underrepresented group. You’ve been expected, for so long, to put the comfort of those with more privilege ahead of your own. It might be the only way to survive an organization. And the pressure to conform in the system is only greater if you are given any formal leadership responsibilities.

Zoom out. Zoom in.

That’s a heavy bomb to drop in a post about leadership. But I’ve shared the notion of patterns repeating at every scale across a system before. The idea comes from quantum behaviour and the Lewis method of deep democracy. So I often look for the types of patterns that I can understand across society and reflect on how they show up for me in my daily life. In my initial reflection on leadership, I talked about how leadership shows up in me, my team, my larger team of teams, and my entire organization. So it feels right to zoom in and think about comfort for my own leadership. Then I’ll zoom outwards and see how it might show up at increasing scale outwards from there.

Creatures of Comfort

So lets assume if you’ve gotten this far into this post, that you’re with me. That you understand that many forms of comfort are a choice… even if it’s gone unexamined. Let’s start with a baseline hypothesis that holding comfort as passive default or intentionally is still an act of prioritization. Let me also be clear that I’m not urging those who are marginalized or underrepresented to do more labour in a system that is already harmful to you. This post is aimed squarely at those with power and privilege within a system or organization to notice, consider, and decide where and when comfort shows up, and how it might be holding us back.

At the scale of you

If you prioritize your own comfort as a leader you’re likely holding yourself back. If you’ve ever done any reading about or experienced anxiety you might know that one of the most natural responses to anxiety is avoidance. It takes hard work to overcome that natural instinct and work through it. Avoidance is also a great way to stay comfortable. The problem with avoidance is it holds you in the place where you are. In leadership it stunts your growth or worse you end up going backwards. Its only when we face things that are challenging that we find out what we’re truly capable of.

You might be thinking, “I don’t do that. I don’t avoid things and prioritize my own comfort!” Here’s a handy list of how that might show up in how you lead yourself:

1. You move from one emergency to the next, and that simply doesn’t allow time for examining if your time is being spent in ways that would have the most impact. Sometimes, letting a small issue burn is the only way to get to the things that could prevent future fires. But not jumping in to save every dang thing you know you could fix is hard. It’s deeply uncomfortable especially if you’ve come from an area of expertise where saving the day is the job.
2. You put off having a hard conversation with someone because you know it will be uncomfortable or you’re not sure what the outcome will be.
3. You don’t apologize or own your mistakes when you mess up because you’re ashamed and just hope it will blow over.
4. You stay silent when you don’t understand something because saying “I don’t know.” or “I don’t really get it.” might make you look foolish.
5. You don’t try something new or a different way, because you’re not sure if it would work and it’s easier to stick to what you know.
6. You don’t share something you’re working on because other people’s perspective might change it before it’s done… and that also might make more work for you.

Any of that sound familiar? Spoiler: I’ve done everything on this list at one time or another. All of these things come back to staying comfortable. It’s the antithesis of bold and brave leadership that’s required to transform an organization.

Inside your team

So with that baseline of how our own comfort shows up individually, what does that mean for a team that you’re leading? Well for starters, if you’ve modelled any or all of those behaviours and they can become the team default. You’re effectively setting a pattern that will hold everyone small.

Creating space for important (but maybe not urgent) work by ensuring there’s time set aside for reflection, learning, or other efforts that make a positive impact on future work might sometimes mean that you have to change what you commit the team to. Maybe that feels like letting others down, but also maybe it just means readjusting the expectations of how much one team can handle. Its not enough to tell your team they can pause and make strategic investments… you need to lead the way. If you don’t make the time for this, who else will?

By not saying “I don’t know.” or being willing to try something new, you make it harder for team members to do it. This essentially quashes any opportunity for innovation. Not only that, but it could actually create a situation where nobody really understands something, but it proceeds anyhow because everyone assumed that someone else knew what it meant. Especially in the context of digital transformation, this can have huge implications and consequences.

If you don’t intentionally model the willingness to share work in progress, ask for help, take feedback and critique to make your work better, your team might not ask for the help they need. Then you don’t really have a team do you? Just a collection of one man bands… which defeats the purpose of having a team in the first place. Our teams should be the first and safest place to go for help… and it’s up to us to create that.

Or maybe you’re okay being uncomfortable and you place the the comfort of your team above your own. There are a few traps to watch out when you do that such as:

1. Not having that difficult conversation might mean that someone on your team isn’t getting the coaching, feedback or radical candor they need to grow and excel.
2. Taking things away to solve, or fix, or protect the team from struggle. I’m not saying there aren’t legitimate times to do this, but first ask if you’ve effectively supported people to solve their own challenge? If you do intervene but you don’t share how something get’s fixed it remains a “black box” to the team. They have no way to learn or grow from that opportunity to overcome a challenge.
3. Avoiding dealing with difficult interpersonal situations. This often ends up with one person to left outside the rest of the group, either by their choice or because it’s not safe. Ask yourself if you’ve seen a situation where the aggressor/bully stays and the victim has to self-exclude or leave?

What if instead you acknowledged the hard and uncomfortable things. Explain how you’re working on the things that are yours to take, and encourage and support your team to tackle theirs. Make it explicit what the goals are and what the most important outcomes are. Remind people they can use some time to do strategic things that could make an future work easier. Be clear that people can ask for help from you and from others. Tell them it’s okay if they try something that doesn’t work out… you’ll still have their back, and you’ll figure it out together. That’s not exactly making it comfortable, but its also not taking away the opportunities for growth and learning.

Betwixt and between teams

Perhaps the weirdest dynamics I sometimes observe in a larger organization is the comfort/discomfort between peers or between work units or teams. As much as organizations might talk about being a matrix organization, or integrated teams… it’s a really tricky thing. Especially in the digital government space. There’s a lot of unique skills and accompanying cultures that go with different teams that need to work together, rarely with any official reporting structure that reinforces them as a unit.

Have you ever had the pre-meeting to discuss how to handle the “other team” at the actual meeting? Maybe in this pre-meeting there’s talk of how to maybe just avoid that other team/specialty all together? Yup… institutional avoidance for comfort at a larger scale. Sometimes it makes sense to check in with people to be on the same page, to make sure you’re showing up prepared and that the collaboration is efficient… So I could maybe let those pre-meeting slide.

What is often more damaging is the meeting AFTER the meeting… you know the one in the hallway (okay during WFH its the private chat outside the meeting chat.) Brene Brown calls it “back channeling” or the “dirty yes”. If you’re not saying things in a meeting and it’s because you want to keep a meeting comfortable (for you or someone else) then you’ve just wasted everyone’s time in that meeting.

Another way that defaulting to comfort shows up between teams is in escalation. Especially in a multidisciplinary team where team members might have different reporting relationships, escalation can be the default for working through disagreements or conflict. The best example of leader not jumping for comfort in these escalations I’ve ever seen is a director saying, “That sounds like a really challenging situation. What did the rest of the team you’re working with say about it? How have you tried to resolve this together?” This is a great question. First, it’s seeking to see what the team has already tried and if they’ve just resorted to escalating rather than working through the discomfort of coming together from different perspectives. By sending the team back to do the hard stuff and making it clear that you’ll only escalate as a last resort, it’s actually empowering, even though it’s uncomfortable. But I’ve also seen leaders who love to “handle escalations” they feel status and power in being the person who can “take that away and solve it”. If you catch yourself in that moment, just pause and check.

Leading upwards

Perhaps the place where comfort is the most entrenched as a priority by default is when we interact with those who lead us. Positional power in an org chart is a real thing. And there’s plenty of career advice that says, make sure the boss has what they want and you’ll do well. Don’t get me wrong. There’s some real tangible things that you should be doing for your boss. Show up, help, be prepared, get shit done. All great. But also, there are many opportunities to accidentally prioritize the kind of comfort that will hold you both back from the most productive and transformative work.

Here’s another handy list of ways this might show up:

1. Only bringing solutions, never problems. I get it… but especially if you’ve “solved this” by yourself… or within a small homogeneous group, are you really bringing the best option? Are you just trying to shield your boss from discomfort? I’ll admit this is a fine line. But just make sure you’re also honest about risks, who wasn’t included in solutioning, or if you might not have the whole picture.
2. Guessing instead of asking. They’re busy. You don’t want to bother them, so you just make your best guess and keep going… If you’ve been working together a long time, that might actually be efficient. But checking in for clarification is not something you should avoid because you’re afraid you’ll look foolish. (See also saying, “I don’t know” or “I’m not sure I understand”.)
3. Filtering. Sure, maybe simplifying the noise and distilling to key points is helpful. Especially if both you and the boss have a shared understanding of the nuances. But if you’re bringing forward the work of deep expertise on your team and you’re filtering them (vs coaching them to distill/simplify where possible) you’re risking introducing your own biases and doing their work a disservice. What happens if you let someone over share or misjudge the level of detail? Or *gasp* what if they share something that still has questions or unpolished bits! Maybe the boss gives uncomfortable feedback. Or maybe they get a deeper understanding of the complexity or issues that lead to different decisions? Are you worried about being embarrassed in front of the boss, or helping your team learn how to better navigate a level of the organization for next time?
4. The go between. Is there a good reason not to simply give up your time/space with the boss and let people share their own work? Are you the go between because it feels safer and you can control how the work gets portrayed? If you’re not close to the work, or it’s not your wheelhouse resist the urge to go between. This is true for the feedback loop of praise and critique. Create a way for the boss to share that more directly.
5. Focusing on the comfort of your boss vs the needs of your team. This one is hard. Especially if you’re in a middle management kind of leadership role. Trying to please everyone is the road to burnout. Please don’t do that. But do ask yourself if you are equitable in the energy you’re investing in both directions? Do you avoid telling the boss the team can’t take something on (or something else needs to be dropped) because that would be disappointing? Does your team know what you care deeply about or where your priorities are or are you waiting to take your lead from the boss before you share? If a decision was made higher up that you know the team will struggle with, are you making space for that discomfort without minimizing it? Are you inviting the senior person to articulate the reasons why or making sure the team knows their perspectives were considered?

If you have a boss who’s said, “I only want to be comfortable”, or one who is entrenched in the idea that you work for them and should do as you’re told, bringing tension and allowing discomfort to be part of your leadership might not go well. But maybe, you simply aren’t sure. If that’s the case, you could ask. How can I raise things that might not be comfortable? If I see something I think you need to be challenged on, what’s the most effective way for me to do that? I’d like to give my team more opportunities to hone their skills and your direct feedback (good or bad) is important. How can we make that possible? It might seem like a weird conversation to have, but the alternative is never knowing and erring on the side of caution, of comfort.

Final Thoughts

I saw a tweet recently from someone who said:

I am not the same person I was 2 years ago. I feel like my spirit had a growth spurt and is all awkward and gangly.

This really resonated. It has been a lot. In particular I feel this sense of awkwardness about leaning into breaking the defaults of comfort and how that shows up for me every day. In some ways, craving comfort and easy is understandable. There’s a lot of great advice to take care of ourselves and to be gentle and kind as we forge bravely forward into whatever our new future will look like. But there’s a truth about “self care” I think is getting lost in amongst all the social media self care mantras. Part of self care is putting in the daily work and habits that make us resilient. Drinking water, going outside, getting enough sleep. None of that is insta worthy. None of that is earth shattering… but it is being consistent and doing things we don’t feel like in the moment because they will be good for “future” us.

The same is true for leaning into discomfort… it’s not one big flourish or moment. It’s in the daily, mundane, and ordinary of everyday life that you have the greatest opportunities for impact in leadership. And the good news is, you can start with yourself.

I definitely don’t know if breaking the default of comfort is a great idea for career advancement. But I do firmly believe that without tension there is no growth… in people and in organizations. So I do think it’s critical for leadership.

We need to examine the role own own comfort plays in our leadership. As an invisible default it is holding us back at every level. Most critically, as a society. If we hope to dismantle oppression and white supremacy, we need to start somewhere. I humbly suggest that looking at how comfort shows up in our daily life at work is a critical first step. And if you’re privileged and have the opportunity to lead people in either an informal, or formal way, you owe it to those around you to be willing to at least try something else that could lead to transformation for everyone.