Breaking Free From The Work Trap While On Vacation

Fall’s coming. And as much as I adore this season, my mind can easily turn to the cold that will arrive and vacation adventure travels.. We love our vacations, yet the persistent challenge of working during cherished breaks is as ubiquitous in the leaders I coach as it is with their teams. Disconnecting from work and immersing in leisure is not just a luxury, it’s a fundamental human right. Making it happen may seem simple to imagine, but it’s not that easy to do. So let’s explore some strategies for making time to vacation, what often gets left out in communication before you leave, different styles of vacations and what to do if you’re failing to take a true break.

Streamline, simplify and succeed.

Let’s face it—getting away can be a challenge. After all, there’s so much to do. This is especially the self-talk of those who are experiencing work overload that never seems to let up. If you’re involved in far too many projects to ever consider taking time off to rest and reenergize, then it’s your job to negotiate people’s expectations of your role and streamline their demands. Proactively prioritizing, delegating and negotiating are the skills to put into action to make your working life reasonable and create the pathway to providing your brain with a mental break and stress relief.

Communicate your availability limits.

Once you set the date when you will be off work, it’s up to you to enable others to plan for your absence well in advance. Merely activating an out-of-office (OOO) email alert is too late and insufficient to announce your vacation status to those you work with inside the organization and out.

One partner in a financial services firm was on vacation when his client urgently communicated that there was interest in a company buyout. They hadn’t said anything to him for months prior, but now suddenly they were crushed with preparations and the deadline was imminent, leaving him little choice but to sacrifice a half-day of his time away with family because he was the only one on the team who could do the work.

To minimize surprises in the future, he’s taken to putting a proactive strategy in place. He initiates early client conversations, supplementing the communication of his upcoming vacation dates with a comprehensive checklist of common challenges and deadlines. This serves as a helpful reminder to jog their memory regarding potential impacts of his unavailability. This proactive communication has lessened client surprises and left him with peace of mind that he didn’t leave it all in the hands of his clients.

Expect to be surprised.

Nevertheless, let’s be real. It’s smart to do what you can to diminish the probability that you will be interrupted on vacation by a surprise demand. It’s also realistic to accept that no matter how resolute you are in your desire for uninterrupted bliss, and no matter what you’ve done ahead of time, there will be times when work comes knocking on your holiday’s door. High-stakes situations can arise while you are away that can’t wait for your return, and your team will reach out to you. But here’s the catch—make sure everyone is on the same page about what truly constitutes a “high-stakes” matter. Is it an intergalactic invasion threatening the fate of your company? Or a trumped-up fake deadline that your team has been duped to believe? What information can you provide to your team ahead of time to help them effectively spot the fakes and to triage the real, urgent messes?

Stop temptation with a habit.

It’s problematic to aim to de-stress and truly relax if you are checking your devices all day long and crowding out the benefits of why you took time off in the first place. There’s no chance of interrupting the sources of stress. Self-monitoring is easy for some but not for all. If you have trouble holding back from repeatedly checking for messages from people at work, there are plenty of hacks for you to experiment with. Recruit an ally and empower them to be your gatekeeper. They could safeguard your device(s), maintain the secrecy of your passcode and help you respect a time limit you make for yourself. With their assistance, you can override the temptation to constantly look at work-related messages.

Choose your vacation style.

Not all vacations are created equal. If you want to work during your time off, consider embracing the concept of a “working vacation,” and own it. Maybe you are a digital nomad—working while traveling on “holiday.” Be transparent about your intentions, letting your team know that you will be available to them while also taking breaks for personal rejuvenation. Setting these expectations up front can foster open communication and ease any hesitations from your staff and colleagues who might otherwise shield you from interruptions.

Get out of your own way.

Finally, if you have a pattern that you intend to disconnect but don’t every time, consider that it’s not them—it’s you. You might be getting in the way of your well-earned vacation. Reflecting on what saboteurs are causing you to avoid putting on the brakes is helpful, whether it be the ceaseless need for accomplishments, the driving fear of what could happen when you aren’t working, persistence in the role of the victim or the people-pleaser or a reluctance to put yourself first, to name a few. These saboteurs aren’t fixed for life, but their hold on you can be. They are at the root of your dissatisfaction and explain your unhappiness and frustration. It’s time to recognize them and lessen their hold on you.

Does anyone need evidence that taking breaks from work is a good thing and necessary? They offer relaxation, fill us with positive emotions and diversify our experiences away from the routine. It’s a no-brainer, and yet there are so many things conspiring to take us off our leisure time while away from work. One big one is work itself. Another one is us.

A version of this article was published by Forbes.com. Photo thanks to Priscilla du Preez.

Getting Hybrid Work Right

We’ve had a few years where working hybrid has become a new normal for many. Even so, businesses continue to apply trial and error to get it right. Like all workplace strategies of consequence, we are all learning from our mistakes to get better at it. Here are a few things employers are doing to get the best from in-person and remote work in a hybrid model, and what to guard against.

Leader Bias In The Wrong Direction

Many leaders regularly wrestle with the decision of whether to mandate employees back into the office for more days in a week. I hear this concern a lot. The mistake to avoid is to act on impulse rather than on data. Digging deeper, it exposes leader bias toward in-person work simply because at the root of it, it’s familiar, and they may enjoy it more themselves. Businesses need to ask themselves whether they have promoted people while using hybrid models and whether promotions have included young people and new hires. Leaders must also acknowledge that if the current system is working, there’s no reason not to listen to what employees want.

Making The Case To Come To The Office

Leaders have recognized that if they aren’t able to make the time in the office worthwhile, then all interactions will be virtual. Yes, there’s food and snacks on offer, movie night, cocktails and game nights. But most of all, facilitated, human, in-person connection is what draws people together. People want to experience their teammates in person, but the frequency varies. One pharmaceutical company makes it easy for people who don’t work closely together to meet, facilitating random match-making by lottery over lunch in the office. Leaders there frequently organize cross-functional coffees and provide introductions as a way of offsetting the decline of random encounters and shrinking networks. For many leaders, the new priority has become to check in with employees when they are together in the office and enable connections.

Employers are more choosy about creating moments when everyone comes together, working to be intentional about the reasons why to do it at all. One professional services firm coordinates bi-weekly, in-person team meetings and reserves other in-person encounters for annual planning, off-site retreats and year-end events where celebration and being together is something people look forward to.

A financial investment company regularly has large employee turnouts by bringing people together for networking socials, training and skills development and sessions to promote well-being. Whatever the reasons to invite in-person gatherings, I’ve noticed that smart leaders have understood that employees want them to be designed for meaningful participation. There’s less of a desire for passive entertainment or lectures or information sharing where few are speaking and most are only listening.

Rethinking Meetings

For many, most days are filled with back-to-back meetings, exaggerated by the ease of virtual communication and WFH where the day starts earlier and ends later since commuting isn’t frequent. In fact, we now know that meetings have multiplied in some cases by more than double. Employees have become challenged with blocks of virtual meetings that can become stale without alone time reserved for thinking, planning or strategizing.

There have been plenty of remedies for the relentless challenge of meeting fatigue such as reducing the number of meetings in a week and the length of each meeting, leaving a day free of meetings, mandating meetings to no more than two people and encouraging employees to reserve time without meetings.

Other changes to make meetings productive are the introduction of meeting management training and training people on the power of negotiating boundaries and how to maintain them. Some have mandated intervals between meetings to leave time for casual chats and so the business of meetings starts on time, and others are clawing back early starts and late days in favor of shorter workweeks for less pay, and offering a compressed workweek.

Securing “core hours” is popular—a dedicated block of time typically in the middle of the day when colleagues are available for real-time collaboration and meetings and personal obligations. What businesses and organizations are realizing is that the sacred cows of pursuing increasing efficiency and speed are exacting a high cost on people over time. There are plenty of ways to make work enjoyable without losing productivity by considering alternate ways to collaborate with others and exercise limits to prevent overwork.

Not Penalizing Women

There was a time when flexible work, part-time work and leaves from work were considered “accommodations” that were encouraged for women, but this often stalled their careers and stigmatized them, as they were viewed as more committed to their families than to their work, which hindered their chances for advancement. Hybrid and other flexible arrangements may bring on fewer incongruities between genders as more men opt in. I know of a technology company that goes beyond having a flexible work policy on paper to actively encourage male and female employees to take advantage of the under-utilized opportunities available to them, with assurances that their careers won’t suffer as a result. Early data shows that they’ve been successful with this approach.

As one senior woman leader I know puts it, there’s finally recognition that working less, taking leave and even working from home isn’t slacking off and that most people are happier to have the option to choose it.

There is plenty we aren’t yet doing well, such as configuring office space where use, not hierarchy, is the sorting decision; promoting inclusivity when not working from home; and driving innovation while reducing collaborative overwork. There’s never been a time when high-performance culture did not require flexibility rather than rigidity, and a workplace approach that balances the benefits of virtual and in-person work is no different. The conversation about the future of hybrid work will continue to evolve with input from all areas, bringing people’s best thinking together.

Thank you to Shridhar Gupta for the image. A version of this article was published by Forbes.com on May 31 2023.

The Secret To Productivity Isn’t Time Management

When the only answer to a leader’s personal productivity challenge is better time management, you know that it’s missing the mark. After all, it’s not likely that one causal answer can’t remedy a very long list that amounts to trouble. Leaders bring concerns about broken time management to executive coaching hoping that five dos and don’ts will solve what pains them. It’s can be simpler than that, but it takes some self-insight to succeed. Let’s take a look at the real symptoms behind less than optimal productivity.

We ignore the underlying cause.

All of us procrastinate. Doing something other than what you’re supposed to can be a welcome relief, but getting a fifth cup of coffee and doing unimportant work is not getting you anywhere. You already know that. With hybrid work, the challenge of doing double-duty when working from home makes a single-minded focus even tougher. The clock ticks toward the due date for everyone when they deliberately delay.

Contrary to what most people believe, it isn’t lack of discipline that causes procrastination. We procrastinate when we are feeling a strong emotion about the work we want to avoid and that causes us to put it off.

An engineer in a consulting firm delayed writing a bid because she was aware that if she was successful the requirements would mean undue pressure on her staff at a difficult time when they were already working weekends.

A physician researcher with chronic procrastination challenges admitted to himself that the research he had signed on to no longer matched his interests. He did it for reasons that seemed right at the time, but those reasons didn’t hold.

To address procrastination, you have to look inward. Tune into your thoughts and emotions to better understand what you fear. With the clarity you gain, you are in a better position to give yourself good counsel and make adjustments that relieve whatever is interfering with the work.

We are overwhelmed with collaborative overload.

Who isn’t distracted by unnecessary email, wasteful meetings and demanding requests? Most people believe that this is where we waste the most time at work and take measures to lessen the distractions. It turns out that if you are an average user of digital media, those aren’t the biggest time wasters you can do something about. The culprit is over-collaboration.

Rob Cross has spent decades studying networks. In his book Beyond Collaborative Overload, he writes about the reason leaders become overwhelmed and, ultimately, undermine their success: Many involve themselves in work they shouldn’t be doing, caught in a mess of excessive demands on their time.

Cross’ work made me think of the vice president of marketing I know who joined a project and admitted that he did it to show that he was right all along. Or the vice president of operations who revealed that she went forward in a multi-functional initiative because she was concerned with what colleagues might think of her if she declined. Or the countless others who are pulled to get involved because of the project’s prestige or because they want to show they are indispensable or because they haven’t considered if the project could be better served with others in their place. Diving in to collaborate won’t do you or the project any good if you are tied up with a project that you shouldn’t have become involved with in the first place.

Efficient collaborators are selective because they are attuned to their own triggers for self-sabotage. Strong performers who value their boundaries turn away from their known temptations.

We are focused on distraction management, rather than forming good habits.

Time is a valuable non-renewable resource. Since we’ve come to rely on our electronic devices to serve multiple functions and with the pervasiveness of social media, people know to reign in digital distractions. This is widely known as attention management. It also focuses on productivity as a function of time management.

What’s worrisome is that with distraction management as a lens, people rely on willpower alone. Willpower is a strange thing. In my work with leaders, we design a habit sequence to override willpower because it’s so fickle. Sometimes it works, and other times it fails you. If you have a habit in place it acts like a force field because you are no longer thinking “Should I or shouldn’t I?” You are simply repeating the tiny actions you’ve designed.

We misunderstand willpower.

And that’s not all. In the past, we’ve been told that our willpower depletes over time, and that it’s better to sync up your must-do activities that require your focus for the time of day when you are at your best. Yet Carol Dweck and others at Stanford University found that self-control is as strong as you think it is. If you think it’s less available and easily depleted, then you are right. If you believe it isn’t limited and your self-control can be generated with a good challenge, you are also right. In practice what this means is you can persuade yourself that you aren’t so easily depleted, you’ll do much better at avoiding distractions. A growth mindset provides us with a view that we can replenish our willpower. This has not only changed my mind about willpower, but I can also predict that I can keep my focus when I most need it.

Are there more distractions on your time now than ever before because you are working from home? Maybe. We know that addressing procrastination means looking within to notice what you’re telling yourself. To resist over-collaboration is to first know your weak spots and keep your boundaries firm. And shifting your mindset about self-control can increase your willpower. The maxim of the Ancient Greeks is as relevant now as it was then: Know thyself. No number of time management strategies and tools can hope to replace it.

This first appeareed in Forbes.com. Thank you to Bruno Figueiredo for the image.

Leadership As An Infinite Game

If life is a game, you need to know whether you are playing an infinite game or a finite one. It’s especially true now as we sit still in our homes and reflect on our work and leadership. As Simon Sinek and others have pointed out, if you play the games of leadership and business as though winning is central, then you are playing a finite game. However, if the point is to keep the game going, then you’re engaged in a different game — an infinite one. Forming new habits of leadership is definitely playing an infinite game, and that’s a vital distinction.

It can be humbling when you realize the goal you’ve set for yourself to become a better leader hasn’t been accomplished. We feel worse about ourselves each time we don’t succeed at closing the gap between what we want to achieve and where we are now. It just might be because of the way we come at it.

Consider your last 360-degree feedback report. You studied the feedback, sorted through what you wanted to work on and then began. But here’s the secret that many know from experience but others haven’t yet learned: Goal-setting is overrated.

It isn’t that goal-setting is bad or not needed. It is. Starting with clarity about what leadership behavior you want to work on is vital. You need parameters and to start small. But goal-setting alone won’t get you very far.

Too many people start with the problem and then rush into correcting it. A more effective way to start is with the outcome you want to create. To genuinely create, you need to do better than react to feedback or a problem you’ve identified. So how do you set out on a path to become a better leader without it being a reaction? By getting very clear about the leader you want to be. Let me explain what I mean.

Take me, for example. As a young leader, I knew that I needed to delegate more. There were times that I was delegating, but then I’d fall back on my old habits of doing it myself. With more ups and downs, I did what most people do: I worked harder to ensure I had the right processes in place to make delegating likely. That new approach didn’t stick, either. Then something unexpected happened. I was beginning to lose interest in my goal, likely an expression that I thought my situation was hopeless. So I wrote out all the strategies I was using to see what was missing. Once done, I asked myself whether I needed more strategies. Nope, that wasn’t it. Instead, I refocused by asking myself a fundamental question that eluded me even though it was hidden in plain sight. I considered what sort of leader I wanted to be, and here’s what I learned: I wanted to be a trusting leader. Now I had a workable outcome to aspire to.

As Robert Fritz, an expert on structural dynamics for behavioral change, has written, the way to achieve a goal is to think of outcomes we want to create, not to simply react by thinking about how to remove the problem, because that doesn’t often work. With the insight about the kind of leader I wanted to be as my outcome, I resumed the game with the stakes far higher and engaged in the game far deeper than before.

Don’t Confuse The Scoreboard For The Outcome

Learning is often a game played with goals and scoreboards. Measures are helpful to know how you are doing, but we can often confuse the personal scoreboard with the outcome, and that can lead us to take a detour right back to playing a finite game where it’s about winning.

Many people know the story about Jerry Seinfeld’s productivity hack of marking an X in his calendar for each day he writes a joke and maintaining an unbroken chain of X’s. Even though he has disavowed the claim that it was his system, nevertheless, it’s a great approach for some people. But if the measure of the X’s becomes the goal, as often the measure can if you aren’t careful, it will replace the outcome of becoming a joke-writing comic. Getting and then maintaining a winning streak of X’s isn’t the same as writing high-quality jokes, for example. Too many people confuse the measure for the outcome, and that’s when they get derailed. Getting back to leadership and the skill of delegating, running a perfect streak of days delegating could mean I’ve reached my outcome of being a trusting leader, or it may not if I wasn’t mindful of also matching the work I assigned to people’s strengths and making resources available so they succeeded.

This is where identity-based habits are so vital. Those are the habits we form with deliberation that change our self-concept. The centrality of winning is not the main concern for those playing the infinite game. Playing this game shifts your mindset from winning, a place where you may have started, to building a new habit by deepening your understanding of yourself. It’s a game played outside in the world with new behaviors — and inside yourself, too. You take action while watching yourself, as I did, as an observer at the same time. I wanted to be a trusting leader; what was undermining my trust in others? How could I address it? How could I set expectations well when I delegated? These questions can show up and need addressing.

There’s a powerful myth that strong leaders come ready-made and fully developed. Maybe that’s why people think that strong leaders are born and not made. Yet people are growing around us all the time.

When we look at leadership development as the infinite game it is, with identity-based goals and not as a problem to be solved, we can experiment with who we are and how we show up with greater freedom.

What To Do When You’re Overworked

“No one takes their foot off the pedal when they’re in the game.” 

Be forewarned, this idiom tells us, you need to go full tilt without letting up if you’re going to be successful, meet the deadline, or delight the client. As the belief goes, maybe those people who slow down “just don’t think like champions.”

That’s what a new client of mine said was the reason why he was exhausted at work. It resonated with me because my own work ethic used to be driven in this way. When I used to work intensively for years, I didn’t see the point of pausing or celebrating my milestones. It just slowed me down. When people around me insisted I take better care of myself or leave time for other interests beyond work, I felt they were distracting me from getting things done. My resistance seems nonsensical to me now, all this time later, but for many, this is still their reality.

For so many leaders, keeping your foot on the accelerator is an admonition not to slow down no matter what. Although giving up may not be a great idea, the belief in going without stopping can be dangerous. I’m not referring to the few who end up fully burned out and hospitalized, but there’s an agreement in the workplace that ceaseless change and churn will never stop, and we all know that it’s unsustainable. Just yesterday an executive told me that although it was crazy at work, he was going to take some time off to re-energize because “it never stops.” The charged-up velocity of change has many more people lamenting and asking themselves how much longer they can go on this way. The “slow season” is no longer. There’s only one season — it’s full-on.

Leaders often say that they don’t want to pull back because they want to model productivity. Ask yourself what you are really doing when you stay at work yet again dragging yourself from meeting to meeting with your head down, shoulders rounded, and maybe even shutting yourself away to “get work done” in your office. It’s easy for others to see when someone is working late most of the time and is tired and frustrated. Your emotional skills as a leader are what we know now as a social contagion. This means that if you are grouchy, showing stress and frustration, you’ll soon see it spread and reflected in the culture.

You don’t need an executive coach to tell you that this is real. You or someone you know probably lives this. The question on leaders’ minds is what to do about it. There are many good strategies to consider. Consider these three.

  1. If you’re feeling that you are doing too much, you most likely are. Capture your activities in an audit of your own making, documenting how and with whom you’re spending your time. I’ve observed many leaders discover that they have been over-involved with their team, for example. There’s an opportunity to pull back and nudge your rock stars forward without your full involvement. Too often, CEOs who are new to the role or leaders who have assembled a brand new team have let close stewarding go on for too long. Think about efficiencies for you while nurturing those around you. Where else can you elevate yourself to fly at the right altitude doing high-value work while providing new opportunities for others?
  2. How do you start your day? Do you set yourself up to be hooked by urgent matters? If you’re searching for business problems and urgent matters, as many do, you are looking to be helpful, but ask yourself if your work is really moving forward. Instead, begin with your strategy and then reverse engineer it so that your daily to-do list sets you up to achieve strategic objectives.

A client of mine was a fastidious list maker and then gave it up, priding herself that she could store her to-do’s in her head. It was one thing she started doing before she became a CEO for the first time. Then when she took a job as CEO, she continued to keep much in her head until she realized that she was prioritizing fighting other people’s fires. Without a written list she committed to of what she wanted to accomplish each week and day, she was easily taken off track.

She’s back at list-making now, and it didn’t take much effort to restart the daily habit. They say that our heads are round so our thoughts can change direction. It can be much easier than people imagine. Consider the productivity hacks that have worked for you and assess if it’s time to bring them back. Winging it just means you are receptive to whatever comes up. There’s not much strategic thinking in that.

  1. It’s necessary to give yourself a break, no matter how strong you enjoy your black coffee or how long you claim you can keep going on with little sleep. What often holds leaders back is their belief that they’re indispensable. Don’t believe your own good press. You wouldn’t tell your own team to postpone their vacations indefinitely, would you? Or encourage them to avoid organized social activities at work because it’s busy? Start planning so that you can absent yourself from a meeting or take the two-week vacation you are owed.

Perversely, if you don’t let up, you’re likely underperforming and dragging your people with you.

This article was first published here on Forbes.com. Photo credit: Matthew Henry.

You say you want open debate and disagreement

Creating a climate where people speak out even when there is agreement is something many leaders say they want. A measure of group and team effectiveness is how it approaches diverse points of view. I find it surprising that I haven’t yet seen a team assessment or a leadership competency model that includes the courage to disagree in the face of agreement as a measure of team productivity. It’s sorely missing. The closest we come to it in organizations is the measure of valuing diverse views, but that isn’t quite the same thing. And it isn’t about generating buy-in either: that is easily achieved by complying. So how do you support an environment that is open to dissent? Consider telling a story.

Just today I coached an executive who was looking to create a vulnerable climate in a group so that no one holds back their ideas or disagreements. My client said he knew plenty of classic b-school stories but he acknowledged that these stories were well known and that re-telling them wouldn’t likely move the dial. Greater rapport building was among his chief development goals so we dove in to search and shape a story of his own that would produce the results he wanted for his team, the business and ultimately, the culture. A story in the recent past where he contradicted agreement in the room provided an example of the positive result that was the consequence of his contribution.

Reversing the train by speaking up

One of my current favourite stories of disagreement comes from the political world during a recent US primary election campaign that Alexandria Ocasio-Cortez waged in the district that covers the Bronx and parts of Queens NY. You don’t have to follow politics or live in the US to enjoy the story. There was a lot at stake. With the present decline of democracy in the US, the strong distrust in government institutions, persistent polarization and many disenfranchised people who don’t vote or vote contrary to their interests, another victory for her long-seated Congressional opponent would have meant no change and would have generated greater cynicism about politics. This candidate’s platform was different and what she needed were ways to transmit her non-traditional message. Alexandria faced a formidable opponent in her own party, is only 28, unknown, and this was her first political campaign.

When the design studio began the work on creating her visual identity (campaign signs, logo, etc.) they went back in time to research civil rights movements to learn about how others successfully communicated a candidate promoting great change. Just a few days before their finished design was going to press, someone spoke out that what they had created had to be scrapped. It just didn’t resonate in a powerful way. So they started over and their brand new design went to press. The result, like Obama’s hope poster in 2008 by the artist Shepard Fairey, did the job and helped Alexandria win the primary by bringing out the vote even from those who had traditionally stopped voting. Speaking up to nix the design and recommend starting again seemed crazy so close to the print date. But that’s what was needed and that’s what worked.

One way leaders can support the groups and teams we work with to contribute is by coaching people on the skills of dissent. There are people around us who may want to disagree, but who don’t know how and fear embarrassment, uncertain how their view will be received. At the other end of the spectrum, I once asked someone I worked with how she tempers her persistent tendency to question with a concern about being perceived as too negative and it turned out that she wasn’t aware that it was a risk and hadn’t noticed the impact on others.

Here’s what to keep in mind

This list of tips is as useful for the hesitant and cautious as it is for the outspoken:

  • Get out of your way. It’s not about you. Keep your higher objective in mind and let that fuel your courage to disagree and guide you in thetiming of when to do it.
  • Ask a question rather than be oppositional. Become skilled at influencing and negotiating gently and firmly without raising the heat.
  • State what you agree on. And then present your concerns.
  • Call out the ‘sunken cost’ principle when it’s at play so that the group can review it and change direction.  (sunken cost: continuing down the road even though there is evidence that you need to pivot)
  • Build on what’s being said. Show you are listening and taking other’s views into consideration.
  • An effective way of influencing is to tell compelling stories.

The reason you as a leader invited others to the meeting is because of the contributions they can make and the value they can add. Don’t just tell people you want them to speak up and disagree, coach them on the skills to do it and acknowledge them when they do.