This is hard: Strategies for pushing back in remote projects
I’ve been working remotely for parts of nine years. Most often, the benefits feel boundless.
On the business side of things, it’s allowed us to hire the best person we can find for any open position, rather than the best person in a local area. Personally, remote has taught me to stop striving for “work-life balance” and to just live my life — whether that is moving our family to France and back, or ultra-running, or digging into a complex professional problem on a Saturday night because I feel like it.
But I’ve digressed already.
Despite those benefits, remote has its fair share of challenges, especially remote leadership. At our annual meeting of the YNAB executive team this past January, we took turns building a list of things that irritate us. (It’s a great exercise. We’re a fairly positive, optimistic group, but this sort of Festivus-like airing of grievances was great for surfacing issues.)
On one of my turns around, I volunteered: Remote coordination is hard.
Some would say that’s an understatement. Some would say remote is no way to run a product operation. None other than Marty Cagan, who quite literally has written the book (in this case, Inspired: How to create tech products customers love) on the subject, warns:
I don’t want to paint this as too black or white, but I also don’t want to mislead you. All other things being equal, a co-located team is going to substantially outperform a dispersed team. That’s just the way it is.
It’s my professional quest to be an outlier to Cagan’s argument — but I wasn’t joking at our meeting when I included remote coordination in a list of irritations. Particularly in the early stage of projects, or when breaking new ground, remote collaboration and coordinate is just hard, and not just because of things like time zones and scheduling meetings. Those are easy.
Instead, it is a challenge because it’s harder to push back in remote settings — yet, if we’re doing it right, pushback should play a key part in those early days of a project.
Early days
Imagine you’re leading a new project for a co-located team. You’ve gathered everyone together in a conference room. You’re surrounded by whiteboards and glass-boards, projectors, sticky notes and markers. You’ve told everyone to leave phones at their desks, but bring all the snacks they might need. Pizza will arrive at just the right moment. Every distraction is removed. You’re all there together. You can read facial expressions and tone of voice in every interaction.
Your team quickly comes across a gnarly idea and decides to dive deep. The team hacks at it pretty hard, going around dozens of times, embracing some ideas, discarding others. Everyone is pushing back and questioning assumptions, questioning statements that felt solid five minutes ago. You grab a marker and go to the whiteboard saying, What about this instead?
And, sitting there locked in that conference room, it all feels natural. It feels right. In this scene, hours and hours go by, but it doesn’t feel like it, because this is the way it is supposed to work. The conference room and the whiteboards sent that signal and everyone was ready. (Pass the Red Bull and beef jerky, will you?)
Now imagine that same team, hitting those same gnarly problems, in a remote setting. You could schedule an all-day video chat, but that’s mostly a non-starter as a far as project-starters go (have you every spent “hours and hours” on a video call?). So you work asynchronously, like you always do, in written discussions, comments, and ad hoc calls — which usually works pretty darn well for you.
Except when it begins to not feel natural at all, and you’ve already gone a handful of rounds of raising, discarding, and resurrecting different paths. The discussion that was three hours in the conference room has stretched on for a couple days already, yet it feels like you’ve covered less ground. It’s time to move, but there’s an idea on the table you’re not sure about. It’s an idea that needs pushback in order to see if it is a worthy idea.
Yet you hesitate.
Specifically, you hesitate to raise yet another question. It’s been two days already, after all. And you’re about to make someone explain or defend an idea in writing. Again. Isn’t it time to move?
It happens to me, and I’m not someone who is usually shy about raising questions. I look at the online discussion thread and see that there have already been 32 comments over two days.
It’s heavy.
If you were inside that co-located conference room, those 32 comments and then two-hundred more wouldn’t have felt out of place. I’m not exactly sure why it feels different. It’s not just the time — but I also don’t think it matters all that much.
What does matter is that there is risk here. The hesitation prompted by the feeling of “it’s already been enough” means ideas on the metaphorical table may never get a full test. The lack of pushback means a missed chance to find a problem early, instead of days or weeks down the road.
What to do? There are no quick hacks here — but here are three strategies to help get past — or really, more importantly — stay in this moment.
One: I’m not satisfied
The first one is a prime example of not-a-hack. This isn’t easy, even though it’s simple. Your job is to make I’m not satisfied a welcome phrase. Encourage it. Ask for it. Applaud it. Because when someone isn’t satisfied, they’re raising the possibility that the idea on the table has room to get better. That’s something everyone should buy in on.
Incidentally, this isn’t about being perfectly satisfied. That’s a high bar, and one that it probably isn’t worth shooting for. One strategy I like, when it feels like the decision could be wrapping up, is the question, Is there anyone who can’t live with this? It’s got a much different feel, one that encourages people to raise dissatisfaction if it’s real, but also to measure dissatisfaction against moving forward.
Make questions like this a part of your normal routine.
Two: Test early and often
One way to help someone feel satisfied enough is knowing that the idea or decision in question is going to be tested. This one has rescued me more times than I can count when I’m feeling angst about a direction we’re about to take. Knowing that ending the conversation in that moment means an opportunity to test your options, it’s tough not to be able to live with that.
Of course, this is good advice for any team, co-located and remote alike. Interestingly, though, this is an opportunity that can be easier to miss in the conference-room scene — because in the conference room, you’ve got momentum, and stopping to test feels like breaking it.
The asynchronous, remote rhythm, on the other hand, fits quick-hit testing like a glove. Take advantage of it. Fill in natural gaps in conversation or work with rapid testing, ensuring that when the conversation resumes, you know more than you did before. And when it then comes time to push back, you’ve created space for it, and you’re pushing back about results, not opinions.
Three: Set a minimum deliberation time
This one can feel funny. I mean, I love due-dates. To an irrational extent. What I’m suggesting is that you turn your due date around. Rather than saying we’ll have a final decision on this question by Thursday, instead say we won’t make a final decision on this question until Thursday. It’s a subtle difference in how you frame it, but can make a big one in how it plays out, in creating space for pushback.
This is hard. You’re trying to ship a feature (or copy or a process, or whatever it is). And the strategy I’m suggesting is to set a longer time frame! But the benefit is worth it. If I think I’m holding up our process by raising my nineteenth question, well, that’s a compelling reason not to. But if I know there are two more days on our process no matter what? Then my question or my pushback is just part of the process, not something in its way.
Bonus: Get the team together
Being remote doesn’t mean never being co-located, and as far a I am concerned it’s rarely worth being dogmatic about anything. So when all else fails, or maybe to prevent all else from failing, consider getting your team together for the launch of a new project. It’s not quitting. It’s not giving up on remote work, and it doesn’t mean these three strategies don’t hold water. It’s just one more tool in your kit as a leader, and sometimes it just works.
