What, How & Why, and a Foundation of Trust

I’ve noticed that we spend a lot of time defining the what – what’s the goal, what’s the metric, what’s the next thing we want to accomplish.

I’ve been guilty of this on a personal and professional level. I obsess on goals and defining the right metric to track them. I also see this happen at an organizational level. One thing that always seems to be clear is the what.

The what is an important piece of the puzzle to achieve a goal. Yet, we often fail to see that it’s just a piece, instead, substituting it for the whole. 

The what, I’d argue, is the easiest part of a goal. I could spend all day writing SMART goals that paint a beautiful and vivid picture of what I want to achieve. 

Alas, the what is useless on its own. 

The best leaders provide the what, but recognize that in order to really challenge people to grow and move towards a goal, they need to paint a vibrant picture of the how and why. 

And once the picture is painted, they are relentless in reinforcing it. 

The how tends to be a bit more malleable. There are many ways to get from point A to point B and the route will most likely shift based on changing conditions or ideas from the team on how to do it better (leaders must always be open to feedback from the folks who do the work).

The why, however, must connect to a larger purpose. For the more challenging goals, people must be bought into the why, especially, if it will require sacrifice (of time, energy, or emotional investment). The why must be clear so people understand what their work is contributing to. 

I’ve stated before that people want to be part of a journey. 

The best journeys are aligned deeply with our values. Great leaders see the what as a point on the horizon to reach for but spend more time amplifying the why in order to get people committed to the journey. Once people are enrolled in the journey, it’s easy to engage them in helping to define the how. 

If we spend enough time getting people to buy into the why and ask their help in shaping the how, the what will take care of itself. 

Most importantly, for any of this to work, there must be a foundation of trust in your team. Otherwise it’s easy to hide behind the what and convince yourself it’s all that’s required from you as a leader.

It’s better than you think

Give what you have. To someone, it may be better than you dare to think.

Henry Wadsworth Longfellow

There’s plenty of reasons not to make art or share your gift. 

Others may judge you. Or they may laugh. You could get criticized. Or it may not meet the (unrealistic) expectation you’ve set for yourself. It may fall flat on its face. It could be misunderstood. Nine out of ten people may not see its value.

But (and this is a big but), one person is all you need.

This is the person that needs your gift. This is the person that needs your generosity.

And if there’s one, there’s bound to be more. 

And even if there isn’t, isn’t changing one life for the better still a success?

We all have the power to make an impact. It just requires we replace our fear with generosity.  

Give what you have as best as you can. I promise, it’s enough.

Leadership is a capability beyond ourselves

There are skills in life we pursue because we hope to improve ourselves. 

We exercise because we want to be healthy. We read because we want to be knowledgable. We work on being mindful so we can regulate our emotions. We practice gratitude to find contentment.

Leadership isn’t like these. It’s different from these skills.

Like parenting, leadership is something we grow into. It’s a capability with unlimited potential. 

But, our potential for greatness lies beyond ourselves. We cannot be great parents or leaders on our own. 

Rather, it’s a continuous pursuit to be worthy of serving the people we lead. 

If we don’t calibrate our true north to align with the people we hope to lead, we fail to grasp what it takes to be great.

It takes courage and vulnerability to serve others, to take honest stock of the part you’re playing in building people up or impeding their growth. 

No one is born a great leader or a parent. We learn by having the courage to try, knowing we may fail. And when we do fail, we honor failure with grace and a strengthened commitment to our responsibility. Because our failure isn’t ours alone, but impacts those we lead. We must own our part and reflect on how we can do better. 

We may not yet be worthy, but it’s the only way forward. 

It’s how we strengthen our capacity to be a great leader or parent.

A lesson in getting re-hired on a daily basis

In a split second, we all saw something was wrong. Our friends’ face showed it all. 

I was taking part in a weekly virtual co-working session, known as GoGoDone. The premise of these sessions is to virtually connect with others looking to accomplish some work. We share what we’re planning to get done, break off for 25 minutes to work on it, regroup for 5 minutes to share our progress and repeat for two more sessions. It’s 90 minutes of focused and productive work with a community unlike any other.

Whatever our friend had planned to accomplish during this session was about to take a back seat to the fire drill that had just landed on her lap.

At the end of the session, for our final regroup, she seemed relieved, a weight had been lifted. She and her team had resolved the issue that had popped up unexpectedly. 

In recapping the event, she said something that showed her wisdom as a leader and that resonated with me:

"I always try to remind my team, it's important to show up with your best self, do the work and contribute. But, we get re-hired by how we deal with problems. How we use the opportunities to strengthen our relationships with our clients. Because problems will occur, and how we deal with them is a chance to show our value."

This was a brilliant lesson and I appreciated her generosity in sharing it. 

In business, much like life, we work to present a polished, glossy narrative that shows us in our best light in order to convince others to choose us. But, life isn’t our best marketing material. Life and work are messy, complex and not always straight-forward. 

It’s not enough to convince others to choose you. You have to remind them why they should continue choosing you. 

Proving you are skilled, graceful, calm and confident at solving or resolving challenges is a good place to start. 

Rest and our responsibility as leaders

This past week I turned 37. 

In preparation for turning another year, I decided to take the whole week of my birthday off and use it to engage in the things I love the most. I wrote, I read, I reflected, I hiked, I spent time with my daughters, wife, and friends. It was intentional, regenerative and peaceful.

It was so powerful that I intend to make it an annual tradition. 

When I shared my plans with friends and co-workers, there were several that commented “how nice it must be to take a full week off,” or “I wish I could take a full week.

I’m sure some of those comments were said in jest, but some felt like conditioned response. And if so, what does that say about our culture? Why is the idea of taking time off to prioritize self-care and recovery considered such an outlandish idea? 

If you are a leader within an organization, this is something we must commit to changing. Our people are our greatest asset and this should be considered an investment in their health and well-being.

Thankfully, I work for a wonderful, empathetic company, Businessolver, that encourages employees to take time off – they even rolled out unlimited PTO earlier this year. 

But, what’s interesting is that even before this occurred, I noticed co-workers rarely used all their allotted PTO for the year. 

This is completely unacceptable. 

As a leader, it’s our responsibility to find out what’s preventing our people from taking time off and help them to make it a reality. That may also include self-reflecting on how you take time off. If you are unable to disconnect for a week’s time, what signal does that send to your team? Are you responding to emails while you are out or are you setting appropriate boundaries?

I know the feeling of thinking YOU are the only one who can do the work so you couldn’t possibly take time off.

But, suppose you were to quit or get hit by a bus, I would bet the work would still get done. You’re important, just not THAT important. 

It may feel like working is the right choice to do in the moment, but what’s the cost of doing so – what are you sacrificing? 

Remember, work is an infinite game – no one wins work, the point is to keep playing as long as possible. 

Sustainability is a balance of hard work and effort followed by periods of rest. 

We need leaders who are willing to push back against hustle culture and set the expectation that rest is not a luxury, it’s a necessity to stay in the game for the long-term.

Inspire Up

As a formal team leader in my current organization, I’ve been thinking a lot on what it means to lead. Does the the natural hierarchy of an organization both influence how you lead and obfuscate less evident opportunities to lead?

If you have a team, the natural inclination is to lead down.

This one is obvious. This is your explicit responsibility. We focus on what we’re accountable for and that’s developing our people. 

The slightly less obvious, but still implicit, responsibility is that you lead across. 

You look for peers that are willing to do the difficult work of changing the culture or making a contribution to the larger organization. You build a tribe of leaders at a similar or higher level that you can challenge the status quo with and learn from. You push them as much as they push you. 

The least obvious and oft ignored opportunity for leadership is leading up. This is especially important if there are leaders you admire and hope to learn from. 

In your role, you probably look to these leaders for guidance and direction. But, just because they are higher up on the leadership hierarchy doesn’t mean they have all the answers. Just as you don’t have all the answers for your team. 

The way to lead up is to be the person you would like to see from those on your team. Exemplify your ability to be coachable, provide feedback and challenge the status quo. Offer solutions and don’t just present problems. Demonstrate the paradox of leadership – the ability to lead confidently AND the humility to acknowledge you don’t know everything. 

This openness and curiosity does two things. 

First, it keeps you in a posture of learning, which is the foundation of growth. 

Secondly, when done consistently and genuinely, it builds your reputation as a leader. This makes it exponentially easier to find mentors and teachers in an organization. 

In my experience, we all have a universal desire – to make our short time on Earth mean something, to make a positive impact, to leave behind a legacy. 

Those above you are no different. 

The best leaders want to share their experience and knowledge. But time is precious, so they will be selective of who they invest their time in.  

When you lead up in this manner, you signal that you take your growth seriously. You are a worthy student. 

As the saying goes, “When the student is ready, the teacher will appear

The ability to demonstrate a desire to learn from and put into action their generous wisdom inspires them to reciprocate by becoming invested in your growth.

They make a positive impact, you grow.

This is the very definition of a win-win.

This is the art of building meaningful relationships. 

Jim Collins wrote it best when he shared advice he’d gotten from his mentor. He asks, “How do you know if you’re in a great relationship?” His mentor, Bill Lazier, responded, “If you were to ask each person in the relationship who benefits more from the relationship, both would answer, ‘I do.‘”

The Paradox of Busy

Busy is our default. We justify busy because it keeps us in motion. In a culture that rewards achievement, we equate busy with progress. We hold tight to busy like a security blanket even when it isn’t necessary. 

When we do slow down, it comes with a feeling of guilt or a thought that “I should be doing more.” When we don’t bake stillness or recovery into our existence, it can feel foreign, awkward and insecure. We find that we have no idea what to do with it.

Eventually, we return to busy.

This obsession with busy and the detriment it has on the culture isn’t a novel idea. Smarter minds have written about it. But when we frame something as toxic, it can trigger shame and cause us to over-rotate. 

Like dieting, we can yo-yo between busy and stillness. And like dieting, swinging between both ends of the spectrum isn’t sustainable and gains are short-lived.  

I’d argue there is nothing wrong with busy.

Busy is only toxic when it isn’t balanced or is without purpose or intent. 

Parkinson’s Law states, work expands to fill the time allotted for it. The key is learning to make space for stillness and busy by constraining the amount of time we spend on both.

Too much stillness feels boring and meaningless. As with dieting, we over-restrict ourselves thinking this type of extreme will help us compensate for our imbalance. Eventually, we feel unsatisfied and the itch to contribute begins to appear.

We revert back to old habits and binge on busy. This leads to exhaustion and burnout. We let things slip and fall short of making our highest level of contribution. 

This is the paradox of busy. 

Without intent driving us, we accept our current state as gospel and fluctuate between extremes. 

Busy and stillness are opposite sides of the same coin. 

Our level of busy will define our level of stillness. Our level of stillness will define our level of busy. If we’re constantly feeling out of balance in one, we’ll be out of balance in the other.

Intent makes the paradox evident. It helps us discern and eliminate the unnecessary things keeping us busy so we can focus on what’s most essential. 

A balance between moments of busy and stillness are necessary to contribute in a meaningful way. 

There is no winning, no competition and no award for busy. However, finding a balance keeps us in the infinite game so we can continue to come back and attempt better.

The Hard Thing About Trust

Trusting others can be scary.

Trusting yourself can be terrifying.

As a recovering high-achiever, I thought I had this trust thing figured out. But trust is something that can be glazed over when you are an individual contributor. It’s possible to juggle your work without really trusting others. 

Let’s pretend that trust is a delicious flaky cherry pie. 

As an individual contributor, it’s easy to keep the pie to yourself – there’s only one and it’s decadent.

Why would you want to share it?

There may be times you have to dole some out – a piece here or there – to get support and put your trust in others. But, by and large, you still get to keep the majority of the pie. Each incremental instance that requires sharing the pie is carefully weighed. Do you share the pie, is this person worthy of some pie or do you just save it and do what needs be done by yourself?

The pie is finite and there is only so much to go around. Share too much of it and you put yourself at risk of coming up empty.

This may feel like you are trusting yourself, but I’d argue it’s more a fear of trusting others. 

Leadership, on the other hand, requires you to see the absurdity of the pie, and rethink trust altogether. You can think of trust as a fork in the road, a decision to make about how you want to view the world. 

Down the path of learning to trust others, you assume someone is not trustworthy until they’ve proven they are worthy of your trust.

Down the other path of learning to trust yourself, you assume someone is trustworthy until you have irrefutable proof they are not. 

Assuming trust requires vulnerability because it puts the responsibility of building trust on your shoulders. Someone needs to open the bid. Leaders do so by taking the risk to trust others first. They recognize there is more upside traveling this path. 

Most people aren’t used to being trusted. This lack of trust drives the best people away. 

When you no longer have to face an uphill battle to prove you are trustworthy, you tend to feel energized and motivated. Most people just want a chance to prove they can be trusted to do great work. 

Leaders see the pie as infinite. There is no point in hoarding the pieces. We trust people won’t let us down. In the end, we have faith that the generosity of our trust will return exponentially, for both ourselves, and more importantly for the team and the culture. 

As a leader, establishing trust as part of the culture is the foundation to build other great leaders. It doesn’t happen overnight. It can often feel like you aren’t making any progress. 

It’s in these moments it can be hard to trust yourself, to trust that you have chosen the right path. In the lull, loneliness may appear.

But remember, trust is a long road – paved brick by boring brick. It’s built by finding opportunities to live this value daily, when stakes are low but eyes still on you. 

Trust is a commitment realized through our actions.

It won’t always feel like you are on the right path.

But that’s the hard thing about trust, it’s not a short-term fix with a reward at the end. There are no shortcuts, it needs to be part of the foundation. 

Take the Lead

There is no doubt.

And yet, the tension of fear isn’t shy to remind you of its presence.

This is your journey. Your path forward is clear.

And yet, the next step can be one of a million options.

But the path requires unwavering faith in yourself.

An immutable belief in the end of the story.

Yet, we live in the here and now. Always grounded firmly.

With our eyes on the horizon.

Ready to face whatever is before us no matter if we’re unsure how to face it.

Certainty in the How is a fools errand.

Certainty that we can and will, however, is required.

We must persist, never straying from the pull of the path.

Ever forward. No matter what.

There’s no guarantee it’ll work (yet). 

But it might. 

We try again.

Yet slightly different, a little bit better.

It’s the only way we’ll know if it works.

When it does, we persist.

When it doesn’t, we reflect and learn.

Failure is a data point not an adjective to wear or a feeling to embody.

This is how we lead the dance with fear, rather than let it lead us.

We must learn to lead if we ever hope to share our contribution.

See Below. Thoughts?

We’ve all sent emails like this. We’ve all received emails like this. 

I know I’ve been guilty of it.

It may seem like a shortcut.

But it’s important we see it for what it is.

It’s lazy thinking. 

It demonstrates that I haven’t done the hard work of attempting to understand what’s relevant and making my ask clear.

If I can’t explain what I need clearly and succinctly, then I don’t understand it.

It’s ok to not understand. If that’s the case, take your best guess. 

At least make an attempt. Show that you’ve wrestled with the idea, at least a little bit. And share what you think it means. 

You may be wrong, but that’s how you learn.

When you invest energy into understanding a problem, you become invested in the solution. You’ve put yourself on the hook. 

And when you are on the hook, you tend to care.

Show that you care.

It may seem like a little thing. 

But, as the old adage goes, how you do anything, is how you do everything