Strategy, brainstorming facilitation, and CEO coaching in Ojai, Ventura, Santa Barbara, Los Angeles

Posts tagged ‘leadership’

One-to-one meetings (sometimes called a One-on-One, or 1:1 meeting) are a staple in almost every manager’s calendar. They’re a fundamental pillar of effective management, and a key tool for driving performance. I believe it’s one of the most important tools you have at your disposal, and if you could only do one thing to improve your team’s performance, it would be to make better use of your one-to-ones.

From handling difficult conversations, to turning up unprepared, there are a number of pitfalls that managers fall into. So how can you ensure that your one-to-ones are actually effective? How do you get the most out of them?

Here are a few ideas drawn from my own experience as manager, and coaching first-time and experienced leaders alike. But first, what exactly is a one-to-one and why is it important?

What Is a One-to-One Meeting?

A one-to-one meeting is a regular, scheduled meeting between a manager and their direct report. You’ll meet to discuss progress, ongoing priorities, and roadblocks anywhere from 45 minutes to 1 hour at least twice a month, if not every week. It can be intimate and free-flowing, but as a manager you need to make sure you cover a baseline of topics, and are asking the right questions for both you and your direct report to get the most out of the meeting.

It’s also important to remember what a one-to-one is not – it’s not a status meeting. You should have other systems in place, such as team meetings, project tracking, and status emails that tell you the overall status of ongoing projects. A one-to-one is about developing your team and uncovering roadblocks, not getting updates.

Why Are One-to-One Meetings Important?

One-to-one meetings are crucial for effective management because they’re the foundation of regular communication between you and your employee. They provide a space where you can learn about their work, share feedback, and coach them on what’s working well and what’s not. This regular communication is crucial for building trust and addressing any issues that might adversely impact their progress.

One-to-ones are also an opportunity to develop your employee’s career. Employees usually have goals they’re working towards, even if they are not documented in a formal performance review. One-to-one meetings provide space to talk about these goals and support your employee on their path to success.

The outcome of one-to-one meetings is actionable next steps for both parties. You will leave the session with a clear idea of what you need to do to help them progress, and they’ll be more aware of your expectations for their role.

How to Structure Effective One-to-One Meetings

Effective one-to-ones are about creating a space for your team members to give honest feedback on what’s working well, where they’re struggling, and how you can help them perform better in their role.

One of European soccer’s most decorated coaches stated that one-to-one meetings were an integral part of his management style. In his management coaching sessions with Harvard Business school, Sir Alex Ferguson, who won multiple trophies throughout his career, explained how his players benefited from 1:1 meetings – the players thrived knowing they had the ‘coach’s shoulder.’

Having these conversations away from the rest of the team paid dividends for Ferguson’s results on the field. Similarly, engaging with your staff will likely prove equally as fruitful.

Here’s how to ensure your one-to-ones are as effective as possible.

Optimal 1:1 Agenda

When conducting a one-to-one meeting, it’s essential to have a set agenda. Setting an agenda will allow the discussion to flow organically, rather than simply be a status update. Again, if you cycle through the employee’s task list in a one-to-one session, you risk eating up time and failing to identify the real issues, ultimately preventing great results.

The First 5 Minutes

How you start the meeting determines whether you’ll engage in a productive dialogue or whether it will stay at a surface-level.

First, it’s paramount to create a safe environment for your team members, so take care with how you start out the one-to-one – don’t jump into discussing work right away.

Ask about things outside of work. How’s their family? What did they think about the game last night? Do they have any kids? If so, where do they go to school? Life doesn’t start and stop at work, and life outside of work affects how people show up at work.

Good leadership is about showing people they are valued. Ensuring your team feels supported will not only result in a positive work culture but will also encourage them to deliver their best. After all, if your employees feel you’ve got their back, they’ll reciprocate and want to be successful for you and the rest of the team.

Challenges and Roadblocks

Next, ask open-ended questions to understand the key issues that might be impeding their progress. It can be tempting to go into solution mode, but the aim is to prompt the employee to come up with their own answers. You are there to guide and help the staff learn and grow. If they cannot think of any challenges, or are hesitant to bring them up, ask more direct questions such as, “how do you feel about your upcoming deadlines?” or “how are things going with your new hire?”

Current Priorities

This part of the meeting not about getting project updates – it’s about helping your team set priorities. In most businesses, there are more projects and new ideas than there are hours in the day. Even the most disciplined employee can take tangents and get distracted by shiny new ideas. This is your opportunity to talk through their current project list and understand how they set priorities. Some of the best coaching opportunities come from helping your staff align their priorities with those of the business.

Career goals and personal development

Too often managers skip this step, which can leave people feeling like there’s nowhere to grow in the organization, or that you don’t care. Not every meeting needs to talk about career goals (though you should be touching on this at least 4 times a year), but you should be talking about some aspect of their personal development. For example, if they are struggling with having difficult conversations, and have committed to work on it, now’s a great time to follow up – what did they take away from the book you recommended? How did their last difficult conversation go?

The Wrap Up

The final step in a highly effective one-to-one is review the key takeaways and agree on commitments. Ask the employee – “what were your key takeaways from this meeting?”  Letting them summarize the meeting, rather than you, is a great way to see if you’re on the same page. Then ask “what are you are actioning from this meeting?”  Having someone articulate, in their own words, what they are committing to, often has a very different outcome than you telling them what to do.

Avoid Common Traps

There are a few common pitfalls where one-to-one meetings can go off the rails. Here are four to look out for:

Avoid jumping straight to solutions

You know what people say about when we assume things.

This is your opportunity to understand what makes your staff tick, how they think about their work, and what might be holding them back. Don’t assume you know what they are thinking and feeling, and jump to conclusions about what they need. Ask clarifying questions. Dig deep.

Don’t ignore your high performers because they are “low maintenance”

Another dangerous assumption is thinking your high performers don’t need a regular 1:1 conversation. Every member of the team has blind spots. It’s tempting to focus all your time and energy on employees you feel need the most help or might be underperforming. Remember, it is the strong performers that you’re trying to retain. Don’t let yourself fall into a situation where key players exit the firm due to a lack of engagement from higher management because you labelled them “low maintenance”. 

Show up

Be present. One-to-ones only work when you devote your full attention. Silence your phone and close your laptop. Try to use a paper notebook so you’re not tempted to look at your emails and Slack messages. Try not to be thinking of the next thing to say, and try not to dominate the conversation. If you’re talking more than 50% of the time, it’s an at-versation, not a conversation.

Try not to take on their work

Employees who fail to follow through on objectives might try to shift the blame, or shift the responsibility back on you. For example, ‘I haven’t got the answer I need from marketing, can you help?’ The team member is putting the onus on you to fix the issue. Don’t let them put that responsibility on your back.

Teach your team that they are ultimately accountable for the work. If they are not getting the answers they need from other departments, or from clients, it’s on them to follow up relentlessly to get what they need. If you start taking on that responsibility, not only are you teaching them that they have an out, but you will ultimately become the bottleneck as you chase down issues for your team.

Final Thoughts

We hope this article has been enlightening, and you can take something away to improve your 1-on-1’s. Remember, the key to having effective meetings is that you are prepared, focused, and present. It doesn’t have to be perfect the first time. Try this agenda, keep these strategies in mind, and iterate your way to success. The most important thing is to make them a priority.

If you are new to 1:1s, or you feel like you’re not getting the most of the 1:1s you’re having with your team and would like to have a focused coaching session to dive deeper into 1:1s, email me at

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I first wrote this article 10 years ago, and recently came across it in my Evernote files. Since then, I’ve graduated from working inside growth companies to coaching CEOs of growing companies, and I’m in the process of graduating from track days and time-trials to door-to-door racing. Reading the article 10 years later, I realized these same lessons ring true, and that I’ve learned a few things along the way, so here’s version 2.0. Enjoy!

I love analogies, but for years I’ve listened to my colleagues in Canada relate every business lesson to a hockey analogy. Everything will work out fine if we just “skate where the puck is”. Working now in the US, everything is a football analogy – “we need more team members who are broken-field runners”. I do enjoy hockey and football, but I barely know the difference between an offside and icing let alone who won the Stanley Cup in ’72. Half of the time the analogy is completely lost on me.

So in an effort to bridge the communication gap, I’ve related my learnings in business to one of my passions – auto racing. I hope this helps other business-minded gear-heads communicate more fluently with their peers, and if nothing else, I’ve laid the foundation for you to take your team to the Skip Barber racing school for “team-building”.

Look where you want to go
One of the deadliest errors, often made by beginners on the racetrack but occasionally made by experts, is called “Target Fixation”. In a moment of high stress, your brain is so overloaded that it becomes fixated on exactly what you are trying to avoid – gravel in a corner, an obstacle, or another car. You end up hitting it square on.

In business, it’s very easy to get fixated on what you don’t want – losing a key customer, a market downturn, your best performer leaving. More often than not, you run straight into what you were trying desperately to avoid. It almost happened to me in a previous business in the so-called “Great Recession”. Around 2009, our pipeline was drying up, and in a sombre management meeting, we told ourselves “I guess we’d better start planning to downsize”. Luckily, one of our mentors snapped us out of it. He wouldn’t let us even mention downsizing until we had exhausted every possible option for filling up our project pipeline and hitting our revenue targets. It was every man on deck. He refocused us on the positive outcome, and guess what, we turned it around and headed straight into our best year in history.

To be a great auto racer, you need to have “wide eyes” – you learn to look far ahead, use every corner of your peripheral vision, and look where you want to go. Being a leader is no different – your job is to look further than tomorrow, get a lot of advice and input, and keep your team focused on where your business is headed.

It’s a mental game
Time and time again, I hit a plateau at the race track. I think I’ve wrung every last bit of performance out of my car and driving to my absolute abilities. Then I invite a very fast, very experienced driver to drive me around the track in my car. After a warm-up, they do a few blistering hot laps, a full 2.5 seconds faster than I. We returned to the pits, review the session, and he sent me on my way. The very next lap, I was 1.5 seconds faster, and the next 5 laps I was consistently 2 seconds faster than my previous laps (I’m still chasing that last few tenths, and that’s what makes racing so fun). It wasn’t the car, or even my abilities that was slowing me down – it was my mental model of what was possible.

Success in business has a lot to do with your mental attitude. Studies have found strong correlations between entrepreneurs with positive outlooks and business success. Most of the time, it’s not your competition or the economy that’s holding you back, it’s your own attitude and beliefs. Those that have an attitude of abundance generally outperform those that believe the glass is half-empty.



A minor shunt. It’ll buff out.

In racing, no matter how practiced and prepared you are, you can suffer dramatic setbacks. Parts break, someone bumps you, or for whatever reason, your perfect setup just isn’t working on a particular track like you thought it would. Even world-championship teams have bad weekends. The best drivers have persevered through dozens of bad weekends. They learn, they adjust, and they go try again.

The business press loves the “overnight success story”. What they fail to mention is that behind almost every business success is years of blood, sweat, and tears. Yes, one day they break through, but often these overnight success stories have been at it 10, 20, or even 30 years before they became a household name. Every business had failed starts, bad sales calls, unproductive employees – you name it. Things that are completely out of your control hit you from left field. The only thing you can do is dust yourself off and keep going. So much of success in business is just showing up and trying. If you’re self-aware and inquisitive, you’ll learn with every setback, and one day you’ll wake up amazed at the progress you’ve made.

Change one thing at a time
There’s a popular business mantra that says “you can’t manage what you can’t measure”. I also believe that to measure change, you can’t change everything at once.

In a growing company, you will always looking for things to improve. As you grow, you’ll find it increasingly difficult to apply measure progress when you’re changing so many things at the same time.

In racing, we only change one thing at a time, and test it’s effect. You change your sway bar settings on one end of the car, and you go test. You adjust your shock absorber rebound, and you go test. If you were to change all those things at once, and you spun in turn one, you’d have no idea what caused it, and lose precious hours going back to square one.

The same is true whether you are changing a business system, or changing an attribute of your product or web site. If you change your customer acquisition strategy, launch a new web site, and restructure your sales team all at the same time, you’ll never know which one moved the needle.

Win together, lose together


Coaching session with

Even at the amateur level, successful racers have coaches and mechanics. At the professional level, teams spend an enormous amount of time learning to work together in perfect harmony. They know that everything, from the pit crew who refuel the car in seconds, to the suspension engineer who knows exactly how to set up a shock absorber for a specific track, have to come together flawlessly to win a race. Lewis Hamilton gets most of the press for winning 6 championships, but what impresses me most is how Toto Wolff and his team coordinate and motivate the hundreds of people that work behind the scenes to build and maintain a winning race car.

New leaders often believe they need to have all the answers. It’s ok to tell your team “I don’t know. I’m not an expert in this area and I need your help figuring this out”. On top of that, there is probably someone, somewhere who has gone through exactly what you are going through who is willing to help. In my career I’ve been lucky to have a few people who were willing to sit down and talk through a business challenge for nothing more than a latte and the promise to pay it forward.

Successful management teams are staffed with people who compliment one another’s strengths, and who think differently from one another – some big picture thinkers, some detail-oriented; some who are engineers and some who have arts backgrounds. Believe me, it’s not easy – you’ll disagree constantly, but in the end you’ll make better decisions because they’ve been dissected from every angle.

The really successful teams invest time and money learning how to communicate better and work better as teams. They set aside personal ambition and break down silos to achieve a shared vision. Like a championship race team, great teams are built with trust, shared respect, and communication.

If everything feels under control, you’re not going fast enough
World champions drive their cars at the very edge of control. A little more steering input, or a fraction more throttle, and they would go careening off into the weeds. It’s a strange sensation, to feel almost completely out of control, but at the same time, completely in control. Legendary driving coach Ross Bentley calls this “being comfortable with being uncomfortable”. The flip side of that coin is that once and a while, you will spin out (ask me how I know).

If you’re an auto racing fan, you’ve witnessed the two extremes – on one hand are the wildly aggressive drivers that lead one race by a half a lap, but crash out in the next one. They burn their teams out and burn their bridges. On the other hand are the backmarkers who are unwilling to be as aggressive as the winners. Champions find that perfect balance – they are blisteringly fast, take calculated risks, but are patient and persistent, tracking their opponents lap after lap, waiting for them to slip up so they can take the pass for the lead.

In business, I’ve seen companies who are unwilling to take risks, and unwilling to live on that edge of controlled chaos, and they usually plateau. I’ve also worked with companies that are in constant chaos, where the leadership team leaves burning bridges, burned out employees, and fried customers in their wake. The perfect flow is right down the middle – taking calculated risks, moving quickly, and working right in that zone where things feel a little out of control.

You’ll never have all the data and all the answers – a napkin-sketch plan passionately executed will beat a perfect plan poorly executed every single time.

Slow hands, fast car

The final, and most difficult lesson to learn for executives and CEOs is to lead with calm, patience, and perseverance. In a race car, it looks impressive to be attacking every corner beyond the limit, sliding the car, hands frantically correcting and sawing at the wheel. Typically this racer runs out of tires, or talent, and loses their lead to someone smoother. The same goes for business. The model we see on TV reality shows is the frantic, yelling CEO, driving everyone to the brink and leaving a wake of destruction. In real life, it’s a marathon. The toughest lessons for me personally, both on the track and in the boardroom, has been to remember to breathe, to listen, to seek to understand, and to slow down time when everything’s feeling out of control. The best leaders lead with grace and build confidence in their team, and are aware of the wake they leave.

And remember, if you’re still stuck on your hockey and football analogies – as Hemingway (or Ken Purdy, or Banarby Conrad, depending on who you ask) once said  “There are only three sports: bullfighting, motor racing, and mountaineering; all the rest are merely games.”

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