I’ve had plenty of business failures.
But no matter how crazy things got, my teams and departments have always had a top-tier reputation to execute. We ship. And we keep shipping. All of it high quality work, day in and day out.
I’ve had to turn around teams, work across a range of disciplines (marketing, engineering, design, HR, finance, sales, etc), multiple business models, and various stages of startups. I also built a $7.2 million dollar business from scratch in 3 years.
Over all those experiences, I’ve developed a set of management principles that I always use. Once I get them in place, all quotas get hit, KPI goals are met, projects get shipped on time, and my team sets the pace for the rest of the company.
All the rules are simple, and I believe anyone can apply them, which is why I’m sharing them today with you.
#1: If Morale is Bad, Put Just One Win on the Board
A few years ago, I was in charge of a Sales department. One month, the team produced zero sales. They delivered a big ol’ goose egg.
This wasn’t an anomaly either, the team was struggling to deliver. They needed to generate dozens of sales per month with a path to 50+, yet they weren’t delivering any.
Many leaders would have stepped in, lit some fires, and made the whole team feel terrible, or fired everyone.
I didn’t do that. I did step in, but I took a very different approach. Instead, I said, “alright, our outreach campaigns aren’t working. We’re going to try something completely different and we have one goal: get a single sale from that one campaign. That’s it.”
And it worked. Within about a month, we had our first sale. Then we had a few more after that. And a few more after THAT. A year later, we were closing about 40 customers per month. Very close to the original goal of 50+.
Yet, if I had held the team to the original goal of 50/month, it would have never worked. The team was beaten down, exhausted, and lacked confidence in everything they were doing. Hence the giant miss of a month that started all this.
When a team (or any individual) is in that negative headspace, even modest goals seem impossible.
During times like this, I look for one simple win to put on the board. Anything to get the momentum back. And I purposely look for a goal that’s a breeze to accomplish.
Then, I nurture that momentum over time by stretching goals a bit more. “Great, we closed a customer. Now we need 5/month.” Then, move to 10, 20, and so on.
With every step, the team gains confidence, gets faster, and builds real camaraderie. Doing this for a year, I guarantee that you’ll be shocked with how far you can go.
This works regardless of what’s causing the morale crisis.
Getting blocked by a mismanaged department? Find a way to get one thing through their convoluted system.
A competitor eating your lunch? Pick one feature to improve and launch it.
No matter how bad the morale or how bleak things seem, put just one win on the board. It always gets better from there.
#2: To Get Team Buy-in, Make a Promise and Keep It
When you join a new team to lead them, everyone is trying to feel you out. They’re asking themselves and each other questions like:
- Is this person legit?
- Are they going to ask for dumb stuff?
- Will they listen if I share harsh truths?
- Can I trust them to look out for me if I go above and beyond for them?
You have a very short window to answer those questions and build a foundation of trust with everyone.
So how do you build trust?
Stephen Covey, author of 7 Habits of Highly Effective People, has said “make a promise and keep it.” That always stuck with me.
During that fluid period with a new team, I look for promises that I can make. Then I move mountains to make them come true. Ideally, these are small things that are getting in the way of your team.
Go to your team and ask them:
“What are a few things in the last week that have really annoyed you? Can be useless work, unnecessary friction, or requests that drive you bonkers.”
Your team will give you PLENTY of ideas if you ask and listen.
Here’s some things to look for:
- Onerous requests from other teams. Some requests will completely bury your team. Often the other team means well, they just don’t have context on the full costs of their request. Go to the other team and figure out if it truly is mission critical. If not, see if it’s possible to hold off.
- Friction with day-to-day tasks. Every software, workflow, and regular task has useless steps. Maybe they made sense at one time but things changed and now they’re unnecessary. Some of these can’t be fixed without a complete overhaul, but some are easy fixes.
- Required tasks that everyone knows are busywork. Reports, regular updates, regular meetings, there’s always cruft that has built up over time. Ask your team which of these they suspect is a waste of their time, then find a way to kill it.
Keep in mind: When you’re fact-finding, don’t make any promises. You’re just looking for a ton of problems and ideas first.
Once you have a list of stuff to fix, go through it and look for items that you’re extremely confident that you can fix. Like 100% confident. Make promises on those. And err on the side of fewer promises at the start.
Make a promise to fix that item, then go fix it.
Do it again and again.
Before long, your team will be feeling relief and they’ll start trusting you. And once they trust you, they’ll follow you through the tough times. They’ll also push hard to keep major projects on track.
Remember: you only have a few chances to make this work. If you make even 2-3 promises and miss on all of them, you’ll lose your team.
Sure, they’ll nod along and tell you that they’re bought in, but they won’t be. They’ll put things on autopilot and stay checked out. You won’t get the results you hoped for.
#3: Break Work into Pieces That Can Be Finished in 2 Weeks or Less
I have redesigned a lot of websites in my career. Some pretty major brands, too. The highest quality redesigns were by far the cheapest and the fastest.
How did that happen?
Pretty simple: we didn’t tackle the whole redesign all at once. We chunked it into small pieces.
Let’s say you’re doing a complete rebrand of a website, that’s a lot of work. But there’s also an infinite number of ways to make it more manageable:
- Can you get the logo redesigned in less than two weeks?
- No? Okay, what about the first draft of a logo in less than two weeks?
- No designer? Can you reach out to 10 freelance designers to see if they’re interested in less than 2 weeks?
- Yes, you can absolutely do that.
No matter how big the ultimate project, there’s absolutely a milestone that can be completed in the next 2 weeks.
In my experience, 2 weeks is about the limit of what anyone can reasonably predict for a deadline.
Anything past that and everyone’s just rolling dice. If someone tells you something can be done by Friday, it’ll get done by Friday.
If someone tells you something will be done 3 months from now, it’ll probably take 5-6 months. And a ton of time will get wasted along the way. Even worse, the adage “work expands to fill the time available for its completion” has become so popular that we just call it Parkinson’s Law. It’s absolutely true.
With large chunks of time, work expands and timelines slip perpetually.
2 weeks really forces someone to break off the next critical step that should get done right now.
There is one major exception to this: large projects with long timelines and major dependencies. Some things take a year and go live during a major launch event. In this case, you might need the Gantt charts and advanced project management stuff.
But even in this case, I’d try to chunk milestones and projects into 2 weeks or less. You’ll have a much easier time getting things back on track when they do waver.
#4: Empower Your Team Members to Set Their Own Deadlines
Here’s my simplest and easiest trick to accelerate your shipping speed: ask each person to set their own deadlines.
What? Won’t they just sandbag the due dates and give themselves plenty of time?
In my experience, they don’t. In fact, people will set deadlines that are WAY too aggressive. Even when I’m aware of this, I still do it to myself: “I’ll have that done by Thursday.” Then Wednesday rolls around and I have a mad dash to get it all done.
It’s also one thing to push for a deadline set by your boss, it’s another to push for a deadline that you’ve set yourself. You can’t complain, externalize, or cut corners. You agreed to it so time to buckle up and get it done.
As Daniel Pink recommends in his book Drive, make sure your employees have autonomy, mastery, and purpose. Having folks set their own deadlines is a very easy way to give them a ton of autonomy.
Overall, your team will push a lot harder to meet all their deadlines when they’re setting them.
This does require a few things to work:
- You need to have the trust of your team. If you haven’t built that up by making and keeping promises, your team won’t feel motivated to reciprocate. And the more trust they have in you, the harder they’ll push.
- This does work best for work environments that can be managed with flows (like Kanban) instead of really intense dependency plans. I realize this may not be an option. Even if you have tons of deadlines to sync across teams, I’d still work to get buy-in by having teams sort out deadlines amongst each other with yourself as the mediator.
- Your team does need to consist of solid folks. If you have one of those rare people that externalizes everything, makes excuses, and never ships on time, this won’t work. In my experience, nothing does. The only play is to get them off the team. More on this below.
Combined with my rule to chunk projects into scope that can be done in 2 weeks or less, this builds a very stable operating rhythm across the team. Pick a project that can be reliably estimated, ask the person when they will have it done, they set the date, it gets done, repeat.
#5: Have Daily and Weekly Check-ins with Everyone
When I started my last company, we didn’t have any regular check-ins. No 1:1s, no weekly kick-offs or recaps, nothing.
Makes sense, no need for any of that stuff when it’s just you, your co-founder, and a few contractors.
Then we got to about 4 or 5 employees. And I pushed for adding weekly 1:1s, daily standups, and a weekly kick-off call.
At first, some of the team resisted. We were living the good life as a small company, everyone knew what to do anyway, why add all the extra stuff?
I told everyone: let’s try it for a month and see what happens.
By the end of the month, all the dissent evaporated. Our productivity probably doubled after that.
Why? A few reasons:
- A daily cadence from a daily standup made sure that everyone knew that they needed to get done that day. Then they went and did it. There wasn’t any room to mess around for half a day and then sorta work on something valuable in the afternoon.
- A weekly kick-off oriented us on our key goals and major projects. We knew where the business was at and how our work fit into the larger picture.
- Weekly 1:1s with managers (myself and my co-founder) helped surface any ongoing issues so they didn’t fester in the background.
I have used this template at every department that I’ve managed and it always works: weekly 1:1s with your manager, daily standup with your team, weekly kick-off at the team level or the department level based on your overall size.
I typically only do standups Tues-Fri since there’s already a kick-off call on Mon
Assuming 15 min for a standup, 30 min for a 1:1, and a 1 hr kick-off, that’s only 2.5 hours of regular meetings for each individual contributor. Very reasonable.
So the meeting overhead is quite low and the productivity gains are massive. You’ll notice the change in shipping cadence within a few weeks.
#6: Reduce Your Team’s Goals to 1-3 at a Time
One year, I was running a Growth department. And my CEO asked me, along with the rest of the Leadership team, for each of us to set 7 goals for the year. We did.
It was a disaster.
I think I hit 5 of mine, almost hit the 6th, and missed the 7th entirely.
Most of the other leaders only hit 2-3.
At first, I was a little smug. Then I realized that this whole thing was a complete mess. And even if I hit most of mine, only 1 or 2 actually mattered. How much further could I have pushed those goals if I hadn’t been distracted by checking the box on the other 5?
That’s when I realized that every team and department can only handle 1-2 key goals at a time.
This feels shockingly low. When I was setting goals across an entire company as a co-founder, it felt really scary to go this low. I fully understood why my last CEO started at 7.
The craziest part, everyone FOUGHT me to have more goals. All my department heads, and my co-founder. Everyone was terrified of really getting down to the 1-2 things that actually mattered.
But every time I allowed it, I regretted it. Goals got missed or major initiatives turned into “check-the-box” activities. One of my regrets is not holding the line here.
When your team has one goal to obsess about, the progress they can make on that single objective will outstrip your wildest expectations.
The literature supporting this is deep, I highly recommend reading The One Thing if you haven’t already.
As a team lead or department head, I fully realize your ability to reduce goals may be limited. You might believe in only having 1 critical goal but your CEO may demand 7. So what do you do?
Do what you can. Even if you have 7 goals, try to divvy things up so everyone on your team only has 1 goal.
And if I was pressured to have 7 goals, I’d try to set things up so 5 goals were in the bag but still looked good. Then I’d go spend all my time on the critical 1-2.
#7: Add Ad-hoc Requests to the Queue, Don’t Throw Them on Top
The easiest way to lock up a high performing team? Keep throwing in ad hoc requests that need to be done right now.
So many leaders have a compulsive need to demand random stuff with immediate deadlines.
And their team hops to it.
But at what cost?
Well, the really important stuff that drives the critical goal for the year gets neglected entirely. First it slips, then it’s behind, then it’s dead in the water.
Death by a thousand Jira tickets.
The fix is easy in practice but very difficult to pull off emotionally as a leader. You’re going to want to just sneak that one little thing in. Why not? It’ll only take 5 minutes.
But a hundred little things add up. Without the discipline to postpone the first one, it’ll be much harder to postpone the rest.
So when a random request does come up, I always put it in the backlog.
Then when it’s time to select the next project, maybe it goes to the top of the backlog and gets queued next. That’s fine. But it should sync with your operating cadence, it shouldn’t break it.
Yes, there are occasionally fires where everything gets put on hold for a genuine emergency.
In those cases, break whatever you need to. But this should be rare. If this happens more than a few times a year, you’re most likely leading by crisis.Whenever I’ve been on a team like that, it’s only led to worse results in the long term.
Lean manufacturing had a huge impact on protecting workflows and avoiding expediting work. While this sort of made its way into knowledge work via agile programming, the core lessons are often lost. I highly recommend reading The Goal as an introduction.
#8: Get Ahead of Any Team Member Fires
By doing all the above, you’ll get the team moving. They’ll be shipping at a consistent clip and you’ll be building real momentum. It’s a matter of time before you hit your goals.
I’ve been here multiple times, just to get taken out at the knees.
What happened?
Something blows up with one of the team members. If it’s bad enough, it can completely kill the momentum.
Here’s a few things I’ve been through myself or have seen firsthand:
- A critical engineer leaves just as the team ramps up. The rest of the team is almost entirely fresh. Engineering progress grinds to a halt and the team begins a two-year refactor while the startup loses momentum and ultimately implodes.
- A bonus was negotiated with a senior marketer before I took over the team. Expectations weren’t set well so after the bonus was hit and paid, it was not replaced. Obviously, that person was not happy and ultimately left.
- A senior marketer that managed an entire channel had a junior marketer report to her. They were hired as a pair. When the senior marketer left, the junior marketer also left with her. The entire program for that channel collapsed and never recovered.
If I’m a manager at any level in an organization, I would get ahead of any items like this. First, do a broad career discussion with every direct report. Figure out their goals, aspirations, comp expectations, everything. This will help raise red flags that need to be fixed long before they reach a point where they can’t get fixed.
I also highly recommend that you review your company’s compensation benchmarking systems, all the hiring agreements with your team, and know the compensation philosophy of your company really well. Then look for mismatches on what your team desires.
If someone on your team wants something that the company can’t give them, that’s okay. You just need to figure that out sooner rather than later. Then you can build around that person instead of making them a key part of the team foundation. If they leave at a really bad moment and something collapses, that’s ultimately on you. I know it sucks, I’ve been there more times that I care to admit. That’s why I tend to be way more paranoid about this stuff than I was earlier in my career.
#9: Get Everyone in the Right Seats
This is a bit of an overused metaphor at this point but it’s still really valuable: get the right folks in the right seats on your bus (your business). Jim Collins popularized this metaphor in Good to Great and it still holds true.
Just because your team has assigned tasks doesn’t mean they’re the right ones to do them.
This is also why I spend a bunch of time trying to figure out where people really love spending their time when I’m recruiting. If their instincts match the role well, they’ll easily overperform. If not, performance will be less than ideal.
I always ask folks these two questions:
- What type of work do you really enjoy? Where do you really love to spend your time?
- What type of work do you prefer to hand off to someone else?
These are basically just strengths/weaknesses questions but rephrased in a way to get a real response. If you ask directly for strengths and weaknesses, you’ll get an answer that the person thinks you want to hear. Rephrasing the questions this way gets much better insights. You can also ask people which project they’re most proud of in their career. That tells you where they’d prefer to spend all their time.
I highly recommend that you ask these questions of your team if you haven’t already.
Once you know where someone wants to spend their time and what type of stuff they want to avoid, it’s time to make some judgment calls. Is there enough of a conflict between that person and their role that you need to get them into a different seat on your bus? If they actively hate 5% of their role, it’s probably fine. If they hate 50% of their role, probably time for a change.
Getting everyone into the right seats will have a huge impact on your team’s ability to perform.
#10: Manage the Underperformers and Jerks Out
This is the hardest one and sooner or later, every manager has to deal with it. The sooner you work through it, the faster your team will hit their true potential.
I’ve come across three types of underperformers in my career.
The first is someone that’s just in over their head. They mean will, they’re trying, they’re just not up to the difficulty of the role that they’re in. Sometimes, a little coaching, guidance, and structure is all they need to get back on track. So start there. If that’s not enough, you may have to go the termination route.
The second is the real jerks. While these folks aren’t pleasant, they’re easy to spot. Set expectations with them and if things don’t improve, manage them out of the org. As the famous Netflix Culture deck points out, the “cost to effective teamwork is too high” for “brilliant jerks.”
The third is another type of underperformer that drives the team crazy. They’ll single handedly destroy the morale of the team. And nothing gets fixed until they’re out. This is where the real hit to performance comes from.
It’s a smooth-talking externalizer.
Some people are internalizers, they put all the blame on themselves. This has its own issues at the extreme but folks that always start with “what could I have done better?” tend to make great team members.
Externalizers, on the other hand, put all the blame on something else. Circumstances conspired against them, someone got in their way, personal emergencies were distracting them. It’s always something.
Because they’re so busy blaming everyone else, tons of fires get started around them. Projects fail and other people feel blamed. Things are never working and no one really knows why. It starts to feel like the ground beneath the team is constantly shifting. And it is, there’s always a new story or excuse.
Externalizers that have taken their career pretty far are REALLY good at talking themselves out of a jam.
It’s selection bias, they wouldn’t have gotten to where they are without that skill. So if you lead from a position of empathy and give people the benefit of the doubt, these folks will get a lot of extra chances from you.
The red flag I look for that tells me I’m dealing with an externalizer: the story changes. One lie gets told, time passes, then another lie gets told that conflicts.
If I ever think to myself “wait, didn’t that person tell me something else?” then I know to start paying very close attention. Maybe it’s a misunderstanding. Or maybe there’s an externalizer on the team. Either way I know to keep my eyes out.
Regardless of the circumstances, as soon as you know it’s not going to work out, go to your HR team and figure out your termination process. Document everything, get the approvals you need, and make the changes that your team needs in order to get back on track.
Also, the easy hack to figure out if someone is truly meeting the expectations of their role: ask yourself if you’d rehire that person today. If not, consider making the changes you need to.
