Building a Positive Workplace Culture: When Your Team Is Struggling and You’re Not Sure Where to Start

Let’s talk about the team situation you’ve been hoping will resolve itself.

Maybe it’s the missed deadlines that have become the norm. The low energy in meetings. The friction between two people that everyone is tiptoeing around. The high performer who’s gone quiet. The underperformer you’ve been managing around because the conversation feels too costly. Or just a general flatness — a team that’s functional but nowhere near what you know it could be.

Building a positive workplace culture when your team is already struggling is one of the most demanding leadership challenges there is. And it’s one that most leadership development doesn’t address honestly — because it requires you to do several things at once that are genuinely hard: diagnose accurately, act decisively, hold difficult conversations, and do all of it while still delivering the work the team is supposed to be doing.

It also requires something that’s talked about even less: the ability to stay clear-eyed about your own role in the situation. Because in my experience, a struggling team almost always has a systemic cause — and the leader is almost always part of the system.

Today I’m giving you the framework for doing this well. Not the comfortable version, but the honest one.

Let’s dive in.

High Performance Leadership Starts With the Right Diagnosis

Before you do anything else, you need to get the diagnosis right. Because the most common mistake leaders make with a struggling team is jumping to solutions before they understand the problem. And the solutions for different types of struggle are completely different — applying the wrong one not only fails to fix it, it often makes it worse.

There are four distinct types of team struggle, and they’re worth being precise about.

Type 1: A Capability Gap

The team doesn’t have the skills the work requires. This might be because the work has changed — AI transformation is creating this constantly right now, as teams are being asked to operate in ways they haven’t before — or because the team was built for a previous version of the role. The symptoms are effort without results: people are working hard, they’re trying, and the output still isn’t there.

The response here is developmental, not disciplinary. Training, coaching, pairing with someone who has the skills, or — in some cases — an honest conversation about whether this person is in the right role.

Type 2: A Motivation or Engagement Gap

The capability is there, but the energy isn’t. The team knows how to do the work and has stopped caring about doing it well. This is the flatness I described at the top of this episode — the team that’s ticking boxes but not bringing anything extra. The causes here are varied: poor recognition, misalignment between the work and what people find meaningful, a trust breakdown with leadership, or the accumulated weight of sustained pressure with no sense of forward momentum.

The response here is relational and motivational — and it starts with understanding what’s underneath the disengagement before you try to re-engage anyone.

Type 3: A Dynamic or Culture Problem

The issue isn’t individuals — it’s how the team functions as a group. Conflict that hasn’t been addressed, cliques, a culture of blame or defensiveness, competition between team members that should be collaborating, or a psychological safety problem where people don’t feel safe enough to speak up, take risks, or admit mistakes.

The response here is cultural and behavioral — it requires you to actively shape the team environment, and it’s the type of struggle that’s most directly influenced by how you lead.

Type 4: An Inherited or Structural Problem

You’ve come into a team that was already struggling before you got there. Or the structure — the way the team is organized, resourced, or connected to the rest of the organization — is itself the problem. This is the most complex type because it’s often a combination of all three previous types, and it carries the added weight of history you weren’t part of.

I’ve done a whole episode on inheriting a poor performer specifically — Episode 174. But the broader inherited team challenge is worth naming here because it requires a distinctly different starting point: diagnosis before action, listening before changing anything, and building enough trust with the team to understand what you’re actually working with.

Most struggling teams are a combination of more than one of these types. The reason precision matters is that it stops you applying the wrong solution with confidence. The leader who jumps straight to performance management when the real issue is a culture of blame will make things worse. The leader who runs engagement workshops when the real issue is a capability gap will lose credibility. Get the diagnosis right first.

The Over-Functioning Trap: Why Managing Around a Problem Makes It Worse

Let’s talk about the pattern that keeps more struggling teams stuck than almost anything else.

You know something is wrong. You’ve known for a while. And instead of addressing it directly, you’ve been managing around it. Quietly picking up the slack when the underperformer doesn’t deliver. Smoothing over the team friction instead of naming it. Taking on tasks that should have been delegated because it’s faster to do them yourself than to have the conversation about why they’re not getting done.

This is over-functioning. And it is one of the most damaging things you can do to a struggling team — even though it comes entirely from the right intentions.

Here’s what it costs. First, it costs you: your time, your energy, and your strategic credibility. You cannot be seen as a strategic leader when you’re in the weeds doing work your team should be doing. Second, it costs the team: when you manage around a problem, you signal — unintentionally but clearly — that the problem is acceptable. The team learns that there are no real consequences for underperformance. The people who are performing well start to notice that carrying more than their share is the norm. They start to leave, quietly or loudly. And your best people are always the first to go when the standards are visibly uneven.

Third — and this is the hardest one — it costs you the information you need. When you manage around a problem, you stop seeing it clearly. You normalize it. You lose the ability to accurately assess what’s happening because you’ve become part of the mechanism that’s keeping the dysfunction running.

Managing around a problem is not leadership. It’s maintenance.

The shift from maintenance to leadership is the shift this episode is about. And it starts with being honest about what you’ve been doing and why.

Building a Culture of Trust in the Workplace: Why Your Team Is Not Where You Are

Before you do anything with your team, there’s something you need to understand about the distance between where you are and where they are. And this is the thing I see leaders get wrong most consistently — not just in struggling teams, but in any change or recovery situation.

You have information they don’t have. You’ve been sitting with the problem longer than they have. You’ve already moved through whatever emotional processing the situation required of you, and you’ve arrived at a place of clarity and forward focus. You know what needs to change, you have a plan, and you’re ready to execute.

Your team is at Day One of that journey.

This is exactly what I covered in Episode 250 on leading through change — and it applies directly here. When you’re leading a team through a recovery or a reset, the gap between where you are emotionally and where they are is one of the most important things to manage. If you move at your pace without accounting for theirs, you will leave people behind. The communication that feels repetitive and obvious to you is arriving for the first time for some of them. The conclusions you’ve reached through weeks of thinking will feel sudden and alarming if you deliver them without the context that led you there.

This matters practically in three ways.

First, listen before you act. Even if you think you know what’s wrong, spend the first phase of any team recovery process in listening mode. One-to-ones with every team member. Genuine, curious, non-judgmental conversation about what their experience of the team has been. What’s working. What isn’t. What they think is causing it. What they need that they’re not getting. You will almost certainly learn things that change your diagnosis. And you will build the trust that makes the subsequent changes possible.

Second, explain your thinking, not just your conclusions. When you do start making changes — setting new expectations, having the hard conversations, restructuring how the team works — take people with you through the reasoning, not just the outcome. “I’ve been thinking about this because of what I’ve been observing. Here’s what I’m seeing. Here’s what I’ve heard from conversations with each of you. Here’s what I’ve concluded needs to change, and here’s why.” That transparency is what converts a directive into a shared project.

Third, give them time to process. Recovery is not linear and it is not instant. Some team members will respond to the reset with relief — finally, someone is doing something. Some will respond with skepticism — they’ve seen initiatives come and go. Some will respond with anxiety — what does this mean for me? All of those responses are legitimate, and none of them are solved by moving faster. Building a genuine culture of trust takes time. Your job is to make consistent, reliable progress, not to achieve it overnight.

How to Give Feedback to a Struggling Team: The Conversations You’ve Been Avoiding

Let’s talk about the conversations.

Because most of the time, the difference between a team that stays stuck and a team that turns around is not strategy. It’s not restructuring. It’s not a new process or a new framework. It’s the conversations the leader wasn’t having — and then started having.

There are three types of conversation that consistently make the biggest difference in a struggling team situation.

The Performance Conversation

If there is an underperformer on your team — someone whose output, behavior, or attitude is damaging the team’s functioning — you need to have a direct, honest, and specific conversation about it. Not a hint. Not a softened version that can be misread as encouragement. A clear conversation: here’s what I’m observing, here’s the standard, here’s what needs to change, here’s the timeframe, and here’s what happens if it doesn’t.

Knowing how to give feedback in a way that’s honest without being brutal is one of the most important leadership skills you can develop — and I’ve covered it in depth in Episode 152. But I want to add something specific to the struggling team context: the performance conversation is not just about the underperformer. It’s about the whole team. Every day you don’t have it, the people who are performing well are watching and drawing their own conclusions about what the standards actually are.

If you’ve inherited a situation where a poor performer has been in place for a long time — Episode 174 covers the specific complexity of that — the conversation is harder because expectations have already been set by whoever managed before you. But it’s not less necessary. It’s more.

And sometimes, the performance conversation leads to the conclusion that the fit simply isn’t right. Knowing when to let someone go — and how to do it well — is covered in Episode 172. It’s never the first option, but it’s sometimes the right one. And in a struggling team, keeping someone in a role they can’t succeed in is not kindness — it’s a slow harm to them, to the team, and to you.

The Expectations Conversation

This is the conversation that resets what the team understands about how things are going to work going forward. It’s not a performance conversation — it’s a leadership conversation. It says: here’s what I expect from this team. Here’s how we’re going to work together. Here’s what good looks like. Here’s what I’m committing to you as your leader.

This conversation works best when it’s done with the whole team, not just in one-to-ones. Because it’s not about individual behavior — it’s about the collective standard. And it gives everyone a shared reference point for what the reset looks and feels like.

Be specific. Vague expectations are the enemy of team recovery. Not “I need everyone to be more engaged.” But: “In our team meetings, I need everyone contributing, not just updating. Here’s what that means in practice.” Specificity makes the expectation real and makes it possible to hold.

The What’s Working Conversation

This one gets skipped most often — and it’s the one that determines whether the team believes the recovery is real or just another initiative that will fade.

When something goes well, name it. Specifically, publicly, and in the moment. “What I just saw there — the way you handled that stakeholder challenge — is exactly what I’m talking about when I say I want this team to be at its best.” That specificity does several things: it reinforces the behavior you want, it gives the team a concrete picture of the standard you’re describing, and it tells them that you’re paying attention — not just to what’s going wrong, but to what’s going right.

Recognition in a struggling team context is not about morale-boosting. It’s about calibration. It’s giving people the clearest possible signal of what success looks like, drawn from their own behavior.

How to Retain High Performers When the Team Is Struggling

There’s a specific risk in every struggling team situation that deserves its own moment, because it’s the one that can make the problem permanently worse.

Your high performers are watching everything.

They notice the underperformer who isn’t being addressed. They feel the unfairness of carrying more than their share. They pick up on the team’s low energy and start wondering whether this is a place they want to stay. And because they are your highest performers, they have options. They can leave. And they will — often before you realize it’s happening, and long before it shows up in any metric.

Protecting your high performers during a team recovery is not about giving them preferential treatment. It’s about three specific things.

Acknowledging what they’re carrying. Have a direct conversation that says: I know this team is not at its best right now. I know you’re carrying more than you should be. I want you to know I see it, I’m working on it, and I don’t expect this to be permanent.

Involving them in the solution. High performers want to be part of building something, not just maintaining something. Giving them a meaningful role in the team’s recovery — not more operational work, but genuine leadership responsibility — can be the difference between someone who stays and someone who looks for that opportunity elsewhere.

Being honest about the timeline. Don’t ask your high performers to wait indefinitely for things to improve. Give them a realistic picture of what the next three to six months look like and what you’re doing to make them better. If you can’t give them a credible answer, that’s a signal that your plan needs more specificity.

I covered this in much more depth in Episode 178 on leading and retaining high performers — if your situation involves a real risk of losing your best people, that episode is worth going back to.

And there’s a burnout dimension here too. When a team is struggling, the people who care most — who keep showing up, keep picking up the slack, keep holding things together — are also the ones most at risk of burning out. A struggling team left unaddressed will eventually produce a situation where your most committed people reach their limit first. That is the cost of the maintenance approach over time.

Building a High-Performing Engineering Team and Every Other Kind: The Leader’s Role in the System

I want to spend some time on the part of this conversation that’s hardest to have — and that I think is the most important.

When a team is struggling, the instinct is to look at the team. The underperformer, the difficult dynamic, the inherited mess, the structure that doesn’t work. All of that is real and worth addressing.

But the leader is part of the system.

That’s not a blame statement. It’s a systems statement. If you are the leader of a struggling team, there is almost certainly something about how you have been leading that has contributed to the situation — even if the primary causes are elsewhere. That doesn’t mean you caused the problem. It means that your leadership is one of the variables, and understanding your role in the system is essential for changing it.

Let me be specific about the patterns I see most often.

Avoiding the Difficult Conversation

The conversation you’ve been putting off is, in most cases, the single most important lever available to you. And the longer you wait, the more expensive the delay becomes — in team trust, in your own credibility, and in the compounding cost to the people who are performing well and watching.

Unclear Expectations

If the team doesn’t have a clear, shared understanding of what good looks like, what the priorities are, and how decisions get made, then a significant portion of the struggle is a leadership clarity problem. Not a people problem.

Inconsistency

Teams take their cues from patterns, not from individual decisions. If your standards, your communication style, or your behavior varies significantly depending on your own state or the pressure you’re under, your team spends cognitive energy managing your variability rather than doing the work. Consistency is one of the most underrated leadership capabilities in a recovery situation.

Over-functioning

We’ve covered this, but it’s worth stating clearly in this context: if you are regularly doing work that belongs to your team, you are telling them — through your behavior, not your words — that you don’t trust them to do it. That signal has consequences for both capability development and motivation.

The honest question to sit with is this: if I changed three things about how I’m leading this team, what would they be? Not three things about the team. Three things about your leadership. The answer to that question is worth more than almost anything else in this episode.

And this is also where simple, consistent coaching approaches within your team become a genuine lever for change — not as a program or an initiative, but as a shift in how you interact with your people day to day. Asking rather than telling. Creating space for people to solve problems rather than solving them for the people. That shift, applied consistently, changes team culture in ways that a single initiative never will.

Where to Start This Week

You have a framework now. Here’s how to make it actionable.

This week, do three things.

First, do the diagnosis. Before you take any action, be honest about which type of struggle you’re dealing with. Capability, motivation, dynamic, structural — or some combination. Write it down. If you’re not sure, the listening phase of the next step will tell you.

Second, have one conversation you’ve been avoiding. Not all of them. One. The one that has been sitting at the back of your mind the longest. Plan it properly — use the feedback framework in Episode 152 if it helps — and have it this week. The momentum of that single conversation will change what’s possible.

Third, ask yourself the honest question. If I changed three things about how I’m leading this team, what would they be? Write the answers down. You don’t have to act on all of them immediately. But you need to know what they are.

Team recovery is not an event. It’s a direction. You’re not trying to fix everything this week. You’re trying to establish a clear and credible movement in the right direction — one that your team can see and that your high performers will trust enough to stay for.

That is always possible. Even in the most difficult team situations I’ve worked through with clients. It always starts with the leader deciding to stop maintaining and start leading.

If Your Team Is Struggling Right Now — Let’s Talk

If you’re listening to this and you can see your situation clearly in what I’ve described — if you know which conversations you’ve been avoiding, or you can feel the over-functioning pattern in your own leadership — and you want to work through it with someone who can help you think clearly about where to start:

That’s exactly what a strategy call is for. Not to tell you what to do. To help you get clear enough about your specific situation — your team, your organization, your leadership patterns — that you can take the right action with confidence.

Every month I offer a limited number of complimentary strategy calls to listeners of this show. You can book one at tonicollis.com/lets-chat.

In the meantime, keep leading, and keep changing your team for the better one step at a time.