Creating momentum when an employee is stuck
Many of us are feeling stuck. We’re managing through crisis after crisis, and we’re watching our leaders and our teammates burn out and not be their best selves. I don’t know anybody who’s thriving right now.
Day-to-day, you’re trying to make at least a tiny bit of difference. I see it! You’re working to help people get promoted, you’re running standups to make sure folks have what they need, you’re holding one-on-ones where you check in and see if your teammates are “okay”, for some definition of “okay.”
So what do you do when you’re working with a teammate who is stuck in a cycle of unhelpful or unproductive behavior? You’ve got empathy for them; you don’t want to be a jerk about it. But you still need this person to change course and start moving forward.
I’ve written about how to be directive without being a jerk before, but I’ve got a few more tips to share about approaching this conversation with care.
The “difficult conversation”
Difficult conversations during difficult times is all about balancing empowerment and direction. Imagine that there are levers to pull in every conversation—an empathy lever, a candidness lever, a quietness lever, a bottom-line lever. Your job is to figure out what tools will be effective in each conversation.
I’m going to use a made-up example to ground this in specifics. Let’s say that I need my teammate, Janet, to stop playing devil’s advocate whenever the team is developing a plan of action. She’s always asking “what ifs” to the point where we aren’t able to make decisions about what to actually do. She’s stuck, and the team’s stuck now, too.
We’re debating imaginary circumstances that might never come up because she’s worried about edge cases, and what a bad experience will do to our stagnating customer base. We’re going in circles. Silence would be better than what Janet’s currently doing. We need to ship this thing, and we can’t even get started.
I don’t want to be a jerk, despite how frustrated I am with her behavior. I just need her to stop playing devil’s advocate. So how do I help Janet get unstuck?
Avoid getting stuck by finding your ‘why’.
I need to make sure that I don’t get stuck, too. Without a north star for the conversation—something clear and objective and specific—I risk falling into a trap of endless debate with Janet, where I can’t help her see a new path forward.
Ignoring Janet’s specifics, what I am optimizing for, and why is it so important to me to have this conversation? What’s my most important outcome? What’s my “why”?
It’d be too short-sighted to say I’m optimizing for the team to have a plan when they come out of the meeting. This is a bigger issue than sprint planning. Really, underlying it all, I’m responsible for this team delivering. I need to help my teammates make forward progress so that they can deliver on what the business needs.
This is my why. This is me caring for my teammates: the business needs to continue to exist! We have a crucial product to ship, which will address some of the big feature gaps that our users have been asking for. Having this “making forward progress” goal crystal-clear in my mind will help me ignore all the extraneous context and beef and hubris and whatever else. This is my destination.
When you’re in this situation and trying to figure out your own “why”, really spend time asking yourself what you’re optimizing for, or what you’re trying to avoid. Am I optimizing for speed? Am I optimizing for avoiding layoffs? Am I optimizing for minimizing disruption? etc. Having your “why” clear in your brain will help you avoid being sucked into being stuck, too.
“Stop” isn’t useful without a “start.”
What’s my path to that goal? I need to get Janet to stop playing devil’s advocate during planning meetings.
But “stop” doing something isn’t really helpful, unless there’s a “start” doing identified. “Stop” shuts the conversation down, and usually amygdala hijacks the other person. But I don’t want a fight-or-flight version of Janet: I need Janet to stop asking “what ifs,” and start making decisions.
I need her to actively help narrow down on our plan so that we can take action, not continually increase the scope.
Bring it back to the why: I need her to do this because we are optimizing for making forward progress, so that we can deliver on what the business needs.
Bottom-line it.
“It’s critical that we start making progress on this project. I need you to stop asking ‘what if’s’ and start making decisions, so that we can deliver on what the business needs.”
Notice that these are really simple sentences, just the “bottom line” of the point I want to get across.
Bottom-lining is a really important skill in giving strong direction. If you ramble because you’re nervous, or you want to thoroughly explain, your point just won’t be clear.
Whenever you need to give some strong direction, get the whole thing down to just one or two sentences, max.
Wait, don’t say that yet!
Now, if I deliver this message as it’s written above, is Janet going to hear it? Nope. She’d probably push back, or worse, she’ll shut down.
She’s been playing devil’s advocate in our team meetings for a reason—she’s worried that we won’t catch edge cases, and we might be missing something huge with this plan.
So I’m not actually going to say this to Janet as a first step; I’m going to save this level of bluntness as a last resort if I really need it. What should my first try be?
Janet and I actually agree on the end goal here—that we need to deliver this for the business! We just have different reasons to worry. She’s worried that we’ll miss something big, and I’m worried that we’ll never get started.
Often, a person will push back when you give strong direction, because they don’t feel like their concerns are being heard. You’re trying to switch things up, but their hesitation or disagreement hasn’t been addressed yet.
Acknowledge concerns.
I’m actually going to start by acknowledging her concerns, honestly and authentically!
If Janet is in fight-or-flight mode, continuing to disagree or debate is not going to help me make forward progress. I’m going to reflect back the concerns she’s shared with me one-on-one and in team settings, because I want her to know that I’ve heard her! I’ll literally say to Janet:
“I know you’re concerned that we’ll miss something big. I also know you know how important this project is for the business. That’s why we need to make a change here.”
(If you don’t have a good guess about why your teammate is behaving a certain way, scroll down to some more resources on identifying your teammates’ concerns.)
Stay forward-facing.
Then I can turn this conversation to focus on the future. We’re not going to waste more time litigating what’s happened in the past.
We’re here to talk about what we’re doing from here on out, so that we can nail our most important objective: making forward progress. Delivering this for the business. I’m going to keep reinforcing this.
“Let’s decide what fires we are going to let burn. Let’s make decisions, and start tackling the work, so that we can hit our (mutual) goal of delivering.”
95% of the time, this is enough to help the other person to move forward. They might need to go have a think about what you’ve said (a day to think on it is fine!), but they’ll still agree to try out a new approach. And your one-on-one is a great time to process this and make these kinds of decisions together.
If they aren’t sold, that’s when you reach for your uncomfortably-blunt direction. If Janet doesn’t get on board with this collaborative version, and we keep going in circles during this one-on-one, I’ll use that very clear stop-and-start messaging. Or if I see her return to the same habits in our next team meeting, I’ll ask her to have an impromptu chat one-on-one right away, and I’ll use my stop-and-start messaging then.
This will feel uncomfortable.
Weirdly, I’ve found the prep for these conversations typically feels more intense than the actual conversations. Developing that blunt bottom line is hard. But when I settle in to the actual chat, and the person hears me acknowledge a concern they have, it feels like everything dials down a notch or two.
That’s, of course, if I get the concern right. :)
If you’re not sure what someone’s primary worry is, ask questions (here’s a shortlist of ones to try)! Reflect back what you hear (literally say “It sounds like [repeat what they said]—do I have that right?”). Again, this will take the temperature down a notch. Starting a tough conversation by reflecting back what you know the other person cares about (or is worried about) has never steered me wrong.
Again, imagine that there are levers to pull in every conversation: a curiosity lever, a bluntness lever, a humor lever, etc. Your job is to figure out what tools will be effective in each conversation, and keep trying different tools as you gather more data about what’s working and what isn’t. Each conversation will be different, and will require different tools.
I have a whole library of resources on how to adapt your approach based on what your teammates need, the project and business context, who you are as a leader, and what the organization needs. And a video course on switching between these tools, too. I hope these resources are useful to you today—or that you can keep them in your back pocket for the future.
Want to communicate more effectively?
Check out my Setting Expectations as a Manager video course to balance being empowering and being directive as a leader, and know when to switch up your approach. Or hire me to train these skills at your organization!