The One Question You Should Ask Yourself Everyday

The One Question You Should Ask Yourself Everyday

In your career, it’s easy to get distracted from what really matters. It’s easy to get locked into a cycle of work and lose sight of the point of it all. It’s easy to fixate on problems and processes and projects. And then you wake up from time to time, and you feel lost.

Am I making progress or am I just spinning in place?

Do people actually care about what my team is doing? 

Am I even in the right job? Is this the right company for me? 

I don’t know about you, but I have these “wake up” moments every so often. They can be quite disconcerting. It’s like you’ve been spinning in circles – you’ve been working hard, you’re tired, but what exactly have you been doing? Has anyone noticed?  Are you on a stationary bike or are you headed somewhere important? It’s an eerie feeling honestly, like those strange moments in time when you wake up to the reality of your own consciousness.

If you’re not careful, you can spin in circles for years before you wake up. You can stay in a job for way too long. You can stay with a losing company when there is nothing for you to gain. You can stay loyal to an abusive boss when you should just move on. I see it happen all the time. It’s happened to me. I once stayed in a job for four years when I knew in my heart it was a losing proposition after only four months.

I’m very conscious of this phenomenon. I’m very aware of how easily we can get stuck in bad patterns, habits, relationships. And so, these days, I ask myself the same question over and over again. I ask it to myself and to my team members just about every day.

What do you think that question is?

“Where is the win?”

“Where is the win?”

“Where is the win?”

This is one of the most important career questions you can ask yourself.

It has endless applications. It never gets old or irrelevant. It is the secret to any measure of success I have enjoyed. It seems simple, but its immeasurably powerful in my opinion. So many of us get stuck in situations where a win is impossible or we aren’t clear what win we should be pursuing in the first place.

So many of us take on projects that are not winnable. So many of us focus our energy on time-consuming activities instead of concrete wins. Some of us used to win, but now we’ve taken on more, and we aren’t winning any longer. We traded winning in exchange for money or role expansion or title. It’s a bad trade every time.

The most important career advice I give to clients and team members is to focus on winning. I tell people to seek out wins, to build a reputation of winning. Even if that means taking a step back, changing jobs, reducing responsibility. The most important thing you can do for your career is to build a reputation as a winner. You are better served being a winner on a small scale than being loser on a large scale. Winning is how you build the forward momentum you need to progress in your career. Winning also builds spiritual momentum and energy and confidence which beget even more winning.

One obvious question you must have is, “what exactly is a win?”

Here’s how I think about wins:

Is the reward I can expect for my activity commensurate with the effort I’m exerting?

Are the potential rewards disproportionately high relative to my efforts?

If I’m successful, will anyone know or care?

Does this effort advance me on the path to my larger purpose in life?

Do I find intrinsic fulfillment in doing this irrespective of any discrete reward at the end?

On the surface, this lecture on winning may sound self-evident. Simple even. If it were simple and self-evident, I wouldn’t have to remind myself and others about it nearly every day. I wouldn’t observe so much wasted energy in the workplace. Let’s look at some pragmatic examples of its application to get a little deeper into it.

To leave or to stay?

It’s very hard to leave a job, a boss, a company. Even when your current situation is bad, there is no guarantee the next opportunity will be better. The grass isn’t always greener. Many of us have learned that the hard way. In fact I wrote a blog last year that documents my own thought process when I left my last company. You can read it here.

Too many of us stay in unwinnable situations. In unwinnable jobs. With companies that can’t win. We get lost in the routine, comfortable in the environment, even numb to abuse. I stayed in a job, which by any objective measure was destructive, for four years when I knew after four months there was no reasonable expectation of a win. Believe me, I get it.

But then you wake up one day, as I did, and you’ve accomplished nothing. You’ve become a fragment of your former self, you’ve gone from being a winner to being a loser. You tricked yourself into believing you could win when you couldn’t.

My advice is to ask yourself every day or week or month, “Is this a winnable situation?” If I keep working hard in this job, is there a win in it for me? If you can’t answer “yes” with conviction, you need to find a new path, a new company, a new job.

Going backwards to go forwards

There are many situations where we find ourselves in unwinnable positions. Sometimes we’ve taken on more than we can reasonably expect to succeed at. Other times we’ve taken a job that, by its very nature, can’t result in a win. Sometimes we take on challenges that, even if we were to win in some way, nobody else would care.

Sometimes it makes sense to go backwards to move forwards. I see this a lot with inexperienced managers who get prematurely promoted to run large teams. They can go from being a recognized winner at a smaller scale to a clear loser on a larger scale. It can happen in an instant. When I observe this to be happening to me or to people I manage, I immediately try to find ways to help bring the person back to winning. It’s a tragedy to see a career stall out or falter for no reason other than we’ve placed a winner in an unwinnable situation.

My advice to leaders is to purposely place your top performers in positions that are designed to help them win. The best gift you can give a team member is the opportunity to consistently win. Winning begets winning. If you see someone who was a star, now struggling, pull them back into a winning situation, retool, recharge, and then start moving forward again. Keeping someone in a losing role when they could be winning at something else, is to do them a disservice. It may feel awkward to have this type of conversation with a team member, but in the long run they will thank you.

A path to prioritization

The larger your mandate, the more priorities you must juggle. Most days when I look at my list of things I could do, its daunting to say the least. In fact, if I tried to pursue my full list every day, I’d never win at anything.

When I look at my list in the morning, I do so through the lens of winning. I ask myself, and my team members, which of these tasks are most likely to lead us to a big win. Which of these tasks are going to propel us forward? Which of these activities presents the opportunity for a win that is disproportionate to the effort we would expend pursuing it? I let these activities take priority every time.

You may be asking yourself, well that sounds nice, but what about all the other stuff we have to do but aren’t winnable? My advice to is pursue big wins when you have maximum energy and pursue your table stakes activities when you don’t. I try to pursue wins first thing in the morning and early in the week. Later in the day or week I’ll catch up on the routine things that don’t present me or my team an opportunity for a win.

Outcomes vs. Activities

The dialogue I have with my team is always about wins. I don’t speak in terms of activities. I try not to reward efforts that cannot be directly correlated to a win. To do so, would be to reward the exact behavior we want to avoid. I try to find examples of highly efficient wins – where disproportionately small efforts result in disproportionately large wins. I’m even happy recognizing failed efforts that were rooted in the pursuit of a disproportionately large outcome. It’s about building a winning mindset in your team culture.

My advice to managers is to focus on building a winning culture. Ask yourself and your team the question, “where is the win?”. I think you’ll like the answers you get back.

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