Leadership Lesson #11: Alternate between looking down and looking ahead


Author’s note: This is the eleventh in a series of articles about the leadership lessons learned while hiking Usery Mountain with my 17-year-old son.  Read them all here.

The desert ground crumbled beneath my feet with each step along this stretch of the rocky trail. Despite my sturdy hiking shoes, I still slipped and tripped with unexpected frequency as the pebbles and rocks skittered under my feet. I outright stumbled when larger rocks protruded from the trail.
I looked down along this stretch of the trail.
A lot.
But looking down came at a cost.
The view of the next mountain range was spectacular and every moment my eyes were not on it seemed wasted. The artistically drawn reds, browns and oranges layered upon the mountain range was breathtaking. It’s majestic beauty beaconed. It was hard to take my eyes off of her.
Except for when I slipped.
Or tripped.
With each mini-landslide that crumbled beneath me or rock that unexpectedly jutted up from the trail, my attention was immediately diverted back to my feet.
And then I would miss the view, which seemed to change second by second as the late morning sun danced across the neighboring mountains.
The juxtaposition between needing to look down and the need (and desire) to look up is not different from that of leadership. Great leaders need to look down and look up.
First, leaders need to look up and out at the landscape, which includes paying attention to the industry, the marketplace, the competition and any other environmental factors that might make a difference. It also includes opening themselves to a diverse set of ideas and experiences that might prompt creative and innovative ideas. Not unlike actually hiking a mountain.
A critical part of the leader’s role is to keep a solid eye on the road ahead, including being open to new ideas and thoughts that will help keep a competitive edge, whether that be company-wide or in the leader-from-the-side’s specific domain.
Second, leaders need to look down. Leaders need to look down (and not in the pejorative sense) so they know what’s going on under their feet (in the metaphorical sense).
Leaders need to know the current challenges of the people in their organizations. They need to keep a look out for what is working well and what needs improvement. Where people and process are concerned, leaders need to be in the know.
People are counting on them to know what’s going on, at least provisionally, and when they aren’t in the know, their reputation and leadership capital are at risk.
The recipe: .
: One part looking up to see the road ahead.
: One part looking down to see the impact of your decisions.
: Blend together and serve.

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    Author’s note: This is the tenth in a series of articles about the leadership lessons learned while hiking Usery Mountain with my 17-year-old son.  Read them all here.

    Sometimes on the hike, I could see people far, far ahead of me. With occasional switchbacks and vegetation growing low to the ground, it was easy to spot other hikers, including some that were way ahead of me on the trail, like my son in his neon yellow tank top.

    It was easy to wish that I was where they were. Easy to wish I had covered more ground and faster – remember, my son had a plane to catch – and that I was closer to the summit, just like they were.

    It was easy to wish I was as fit as some of those who were ahead of me.

    It was easy to wish I could hike faster, like my son, whose spirit animal is a mountain goat.

    It was easy to wish I had the hiking boots/clothes/gear of those who were ahead of me the trail.

    But . . .

    Envy has no place on the mountain.

    And it has no place in leadership.

    We are where we are, and that’s all.

    When we drop the need to compare and the feeling that we need to measure up, we step more fully into our own authentic leadership.

    From that authentic and grounded place, it doesn’t matter if

    :  a friend from college produced an award winning film

    :  a colleague who started at the same time is now a Vice President

    :  a fellow grad school student published a book/got recruited by a top firm/ran a marathon

    In fact, from a grounded, authentic place, we can enjoy their victories and accomplishments with them and cheer them on to their next success. Because we are no longer comparing ourselves to them.

    When we stop being concerned with who’s ahead of us, we can bring our focus on ourselves, which is exactly where we need it to be.

    What are my strengths?

    What do I value?

    How am I doing today?

    What do I need right now to be even better?

    Only when we get clear on the answers to these questions, can we be the best leaders we can be.

    And we can be free.

    :  Free from comparison, judgement and pretending to be something other than what we really are.

    :  Free to lead with our own strengths, values and ideals.

    :  Free to be the leaders we have developed ourselves into.

    So don’t worry about who’s ahead of you.

    Stay focused on where you are right now and lead from that perfect place.

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    Leadership Lesson 9

    Author’s note: This is the ninth in a series of articles about the leadership lessons learned while hiking Usery Mountain with my 17-year-old son.  Read them all here.


    When you’re not expecting to be on the sheer edge of a cliff, it is even more terrifying than when you are anticipating it.

    Most of the hike up and around Usery Mountain were of low to moderate challenge.  (If you’ve been reading the whole series, you’ll recall that we had an additional challenge of time pressure: my son’s flight was leaving a few short hours after we began the hike.)

    So when I suddenly found myself with just inches between me and, well, gravity, I was unnerved.

    Of course, I knew I wasn’t going to fall to my death.  We’ve already covered that.

    As I inched along with trepidation and great care, I took a quick glance down. You know, just to see how far it would be if I did fall.

    Big mistake.

    It was much, much, MUCH farther than I had anticipated.

    There wasn’t a switchback 20 feet below. There wasn’t anything below. At least that registered when I looked down. It was like staring into the abyss.

    When you’re doing something that requires great risk, courage and stamina, I propose that it’s best NOT to look down.  At least not at the riskiest, most grueling, character-building moment.  Sure, later it is fine. In fact, then it is highly rewarding to see how far you’ve come.  But at that tender moment when the mountain is steep and when so much is on the line, don’t look down.

    The same is true in leadership. When we are leading through high stakes, high risk situations – whether leading from the top or from the side – it is best to resist looking down.

    When we look down and see the magnitude of the risk we are taking, most of us will get a little scared. Some of us will get a lot scared.

    And whether it takes a little fear or a lot of fear to knock you off your game, you might just act on that fear and pull back a little:

    :  Not execute the plan as big as you had initially intended.

    :  Not run as hard against aggressive deadlines.

    :  Not delegate as much to the high potential staff member.

    If excitement gives way to fear and fear runs the show, you lose control.

    You lose control of strategy. You lose control of tactics. You lose control of control.

    So in those moments of high risk, those moments when it really matters, don’t look down. Instead, keep putting one careful foot in front of the other and take the next step and the next step.

    There will be plenty of time to look down later.

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    Leadership Lesson 7

    Author’s note: This is the seventh in a series of articles about the leadership lessons learned while hiking Usery Mountain with my 17-year-old son.  Read them all here.


    While on the seven-mile hike around Usery Mountain, there were stretches when I could see no one.

    No one on the path ahead of me.

    No one on the path behind or below me.

    With not even the whisper of a breeze, it was quiet. Very quiet.

    I appreciated the silence and the solitude. Mostly.

    But then I got a little lonely.

    It seemed to me that it would feel good to share in the triumphs of overcoming the challenging stretches and to share in the awe and the wonderment of the amazing views. To be in community with someone who was experiencing the same thing I was at the same time I was.

    It was missing.

    I was lonely.

    It reminded me how leadership can be very lonely sometimes. In your organization you might feel a certain peer-less-ness with no one at your level in the organization doing exactly what you are doing.

    No one with whom to share the victories.

    No one with whom to share the setbacks.

    No one to seek advice from or give advice to.

    That’s why leaders at all levels of the organization, not just senior leaders, need to find a peer group.

    Their peeps.

    People who get you and you get them.

    Earlier in my career I felt that sense of peerlessness as Director of User Experience in a large organization. I essentially ran an agency within a corporation.  We did great work and were highly respected.  But I was lonely.

    There were certain topics (struggles, frustrations with bureaucracy, etc.) that I deliberately chose not to share with my staff for reasons of professionalism. And I certainly wasn’t about to share those struggles with our clients, even though we all worked for the same company.  I didn’t have a peer who was doing what I was doing in the organization.

    And there were days when professional loneliness moved in and set up camp.

    Those were the days when it was so important to reach out to my peers outside of the organization. People I could learn from, commiserate with and rejoice with. People I could laugh with over the significance that was sometimes places on such insignificant matters.

    It felt good to be with them and when I reached out, I always wished I’d done so sooner.

    It is lonely at the top.

    Enjoy the silence and the solitude for a bit.

    And then reach out to others.

    It’s okay to be alone once in a while, but don’t go it alone.

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    Author’s note: This is the sixth in a series of articles about the leadership lessons learned while hiking Usery Mountain with my 17-year-old son.


    Approximately two-thirds of the way up to the summit, the path flattened and the seven-mile hike was easy for a stretch. Easier than it had been in a long time.

    My mind, alternating between awe-struck by the beauty of the mountain and distracted by the need to get my son to the airport in just a few short hours, almost missed it.

    It was my body that pointed it out.

    A lighter step.

    A deeper breath.

    A chance to look up.

    My pulse slowed, my breathing got easier, and I began to look out to the stunning views of a neighboring mountain range.

    The shift in my body triggered a shift in my mind.

    And then I realized: I almost forgot to enjoy the easy part.

    That’s what it’s like for leaders, too. We run the risk of failing to enjoy the easy parts when we are in the midst of challenging and difficult work.

    It’s easy to miss the easy parts. We get so caught up and consumed with the trials, tribulations and trauma (and drama!) of our journey that we fail to appreciate and enjoy the stress-free, easy parts.

    The easy parts are when our work feels more like play than work.  We can relax a bit and sink into the terrain more, appreciating the moment and the fluidity with which things are unfolding.

    It’s in those moments that the sweetness of leadership is felt.

    Oh sure, satisfaction is also felt in the victory of a hard fought battle for market share or the race to launch a new product or service. But that’s different. Those aren’t the easy parts.

    The easy parts are when the slope of the path underfoot evens out and the going is good.

    The easy parts are sweet because we get a chance to look up. And in that moment when we pull our head up, we invariably see things we hadn’t seen before: the opportunity to thank a colleague for their help, a chance encounter with someone in our network, or merely the possibility of catching our breath before the next leg of the journey.

    As you push forward, leading your team or yourself to the next milestone, don’t forget to enjoy the easy parts.

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    Leadership Lesson 5

    Author’s note: This is the fifth in a series of articles about the leadership lessons learned while hiking Usery Mountain with my 17-year-old son.

    There comes a time on a hike in the desert when you stumble, perhaps literally, on an unexpected oasis.  When I came across this lush, green patch of grass on the north side of the mountain, I was taken aback. While the grays, beiges and browns are beautiful in their own right, the colors were drab compared to the vibrant hues that sprung unexpectedly from this protected patch.

    If you’ve been following these posts, you’ll recall that my son and I were on a tight timeline: he had a flight to catch in a couple of hours.

    So part of me wanted to rush right past this oasis.

    But the wiser side of me said “Rest a little, enjoy this sanctuary if only for a moment.”

    And so I did.

    And so should you.

    In the midst of harried deadlines and busyness it is easy to cruise right past an obvious place for a rest. When the most powerful currency is time, the rational mind becomes frugal with moments of pleasure. And if we as leaders cannot stop for a few moments and soak in the pleasure, the fruits of our labor, then we must ask ourselves what it is all for.

    This is exactly why we lead.

    For these moments.

    It might be when your team reaches a hard fought milestone.

    It might be when you see a market opportunity and jump on it before the competition.

    Or it might be with someone on your staff: a sales team member who blows away her sales target for the quarter, a new customer service manager who handles a difficult conversation with an angry customer with aplomb, or your assistant who anticipates your needs and adeptly handles situations before they rise to your attention.

    Rest a moment in those moments. Drink them in and let them nourish you.

    This patch of vitality, the lush, green vibrant grass in the middle of the desert, is what it is all about.

    And when we rush by, without stopping for a moment or three to take it in, we dishonor the hard work we’ve done and the efforts and the accomplishments of those around us.

    So take a moment.

    Or three.




    You’ve earned. It.

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    leadership lesson 4

    Author’s note: This is the fourth in a series of articles about the leadership lessons learned while hiking Usery Mountain with my 17-year-old son.

    There are parts of the trail that are steep, where you barely have a toe-hold grip. Your back is up against the cliff wall and speed (see Lesson #3) is not an option. Rather, you must progress methodically and carefully and be confident in your footing.

    The only help available to you is some prickly shrubs, which frankly, hurt more than they help.

    Every step you take feels risky and you begin to wonder what crazy idea put you up on this mountain to begin with. And then you stop that train of thought. Abruptly. Because it’s not helping.

    Instead, you take a breath and find purchase on the mountain. Each step begins tentatively as you ease into it, then becomes confident as you feel supported by the mountain, albeit tenuously supported.

    You suddenly realize . . . you will probably not crash to your death.

    Thousands upon thousands of people have traveled this rugged and rocky path before you. The valley below your current narrow passage is not littered with their bodies.

    No, you will probably not crash to your death.

    As it is on the mountain, it is in leadership.

    As a leader, you take risks. You venture out on the narrow passageway with your back up against the wall. And more often than not, things work out. You score a new client. The acquisition is a success. The unconventional employee you hire thrives.

    Occasionally, however, they don’t work out so well. And do you crash to your death? No. Hardly.

    What happens then? You learn from it. Hard lessons sometimes. You might even call them failures. And that’s a good thing these days. Failure is in vogue. It’s about time!

    The faster you learn from your mishaps, the less likely they are to happen again. And the more transparent you are about your mistakes, the less likely they are to repeat within your organization.

    And when things do work out well after you’ve had your back up against the wall and your footing has been unsteady?

    The rewards are tremendous.

    Sure the accolades from others are welcome, but the real reward comes from inside. When you look back across the narrow path you traveled, with all its inherent risk and potential peril, and truly acknowledge that you made it to the other side (sometimes unscathed), that’s where the deep reward is.

    What are you waiting for?

    You will probably not crash to your death.

    Go take that risk!


    Catch the full series of blog posts of my Lessons on Leadership from the Side of a Mountain.

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    leadership lesson 3

    When you think of doing something safely, images of slow, methodical, calculated action typically surface.

    Safety came in a different form for me on parts of my hike the Pass Mountain Trail on Usery Mountain.

    As I ascended the mountain, it was clear where the sporadic rains had washed away the hiking trail. In some such narrow parts of the trail, the ground crumbled beneath my feet making a hasty decent down the back side of the mountain feel like a near certainty.

    In those places, safety came as speed. Faster was safer, contrary to our typical notions of safety.

    It’s not so different at work.

    You might be racing to be first to market with a new product or service, where safety comes in market share.

    You might be racing to find a new job when something goes terribly awry with your current organization.

    You might be racing to leave a confrontational meeting or a threatening encounter with a coworker to put a safe distance between you and your colleague.

    Speed can make all the difference between feeling like we are in danger and feeling safe.

    Our sympathetic nervous system (the fancy name for our fight or flight response) governs our desire to ditch a situation and look for higher ground (or lower ground when on a mountain!). As part of the autonomic nervous system, our fight or flight response is largely automatic.

    It’s in our DNA to want to stay safe.

    Our bodies and minds have one overarching goal, whether in the board room or on the mountain: survival.

    Only through conditioning the mind and the body to be comfortable with discomfort, to consciously bring about a calm state of being, can we face dangerous situations constructively.

    When we have a handle on our discomfort and can achieve calmness in the throes of discomfort, we can use that discomfort as an important guiding force in our lives, rather than having it rule our lives.

    Leaders need to have self-knowledge and maturity to assess situations quickly and accurately and determine whether the best course ahead is slow, methodical action or rapid, swift action.  Strong leaders can still their fears and quiet their internal dialogue. From that place of stillness, they can see not only market conditions, employee engagement and confrontational colleagues, they can also see beyond market conditions, employee engagement and confrontational colleagues.

    And it will become clear to them whether to speed up or slow down.

    Summoning the calm that comes from years of yoga, meditation and other mind-body practices, I was able to assess the situation as the ground crumbled beneath me.

    On that part of the mountain, faster was definitely safer.


    Catch the full series of blog posts of my Lessons on Leadership from the Side of a Mountain.

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    Before I reached the point of being okay with my son and I hiking The Pass Mountain Trail on Usery Mountain in Arizona at our own very distinct paces, I was angry. Very angry.

    Angry that I couldn’t keep up with him.

    Angry that he wasn’t waiting for me.

    Angry that we weren’t having a mother-son bonding moment on the mountain.

    Angry that his flight back to Minneapolis was leaving in just a few hours.

    Angry that we technically didn’t have time to do the full 7.1 mile hike.

    And most of all, angry that we hadn’t made a plan before we set out.

    How many times has it happened that you assumed the other person was of like mind about a situation when, in fact, you had very different ideas about how things would go?

    I assumed there was no need to make a plan because we would be together. And, based on our speed and the time of day, we would together decide when to turn back.

    If I was with my best friend or my mom, that would have been the case indeed. But there are very few others who can read my mind.

    And so, we set off without an agenda.

    Without a plan, my assumptions took hold and ran the dialogue that played in my head: “I’m the parent here, I should be in charge. I am the responsible one and I need to make sure we get to the airport on time.  He’s flying Spirit so I’ll need to feed him before he gets on the flight. How can I be in charge if he’s a half-mile ahead of me?”

    A simple plan – before we set out – would have alleviated a great deal of angst for me (and eventually for him after he summited and reached the bottom, wondering where I was and whether he’d catch his flight).

    A simple plan would have taken just under a minute to hash out in the form of a few simple if/then statements.

    If we get separated, then A.

    If it is noon and we aren’t at the summit, then B.

    This simple, straightforward plan would have saved me 30 minutes of agony. Fortunately, it was only 30 minutes of agony. Given that he is my son, I’m predisposed toward forgiveness. Given that I quickly realized I didn’t want to waste the day being upset (30 minutes is pretty fast, at least for me), I found peace with our varying paces. And in my shift away from anger and toward the mountain experience, I assumed positive intent: he was just enjoying himself and the climb.

    It is easy to waste an entire day to frustration with our colleagues and clients over assumptions we are making in the absence of a well-communicated plan.

    Here are three steps for turning it around:

    1. Assume positive intent.
    2. Lean toward forgiveness.
    3. Vow never to spend an entire day (or even an hour) upset about something.


    Catch the full series of blog posts of my Lessons on Leadership from the Side of a Mountain.

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    Usery Mountain #1

    Not long ago my 17-year-old son and I went on a hike on Usery Mountain just north of Mesa, Arizona. We took on the Pass Mountain Trail, a seven-mile loop around the mountain which summits about two thirds of the way along the trail.

    It wasn’t a particularly arduous climb but the intensity was elevated for us because we were pressed for time: he was catching a flight back home to Minneapolis in just a few hours. We had less time to do the hike than we would have liked.  As I raced across the mountain, numerous leadership lessons surfaced.

    In the coming weeks I will document twenty of them.  With titles like “You will probably not crash to your death” and “Sometimes it is best not to look down” and “Appreciate occasional and unexpected lushness,” I share the leadership lessons that showed up for me on the mountain.

    These leadership lessons will help you communicate and lead more effectively whether you lead from the board room or the lunch room.


    Leadership Lesson #1:

    Just because you start together doesn’t mean you will end together.

    My son Andrew and I started the hike together.  This was before he told me that his spirit animal was a mountain goat. I didn’t know he had a spirit animal. I didn’t even know he was that, well, spiritual.

    We weren’t three minutes from the trail head when he and his long, lean legs began to outpace me. Considerably.

    For the next 30 minutes, I struggled to keep up. At 6’1” he’s got a solid seven inches on me and it’s mostly in his legs. He’s also got minus 29 years on me.  And while I like to think I’m in shape, this boy runs cross country, cross country skis, and could skip lithely over the rugged terrain in a way I could never do. Not even at his age.

    Those 30 minutes were pure agony.

    I huffed.

    I puffed.

    I willed him to slow down.

    I worried about him.

    I worried about me.

    I tried so hard to keep up.

    I tried even harder not to be mad at him.

    As I saw him round a corner at least a half mile ahead of me, his neon yellow tank top a stark contrast to the greys, beiges and soft greens of the desert terrain, I realized he wasn’t waiting for me to catch up. Loping along at a comfortable pace for his long legs, he didn’t appear concerned with me at all.

    In that moment it hit me: We could both enjoy this hike (which I hadn’t been up until this point!) while being on the mountain simultaneously, each at a pace that suited us individually.

    After this mountainous realization (pun so very much intended), I relaxed my pace and found my groove. I started to enjoy myself and take in my surroundings. And there, in that moment, the first leadership lesson appeared: Just because you start together doesn’t mean you will finish together . . . or should even keep the same pace.

    Whether it is a freshman year roommate, grad school colleague, or someone who started with your current employer on the same day as you, that’s all it means: You started together. It doesn’t mean you are going to keep pace and it certainly doesn’t mean you are going to end together.

    Letting go of feeling that we had to stay together and that I was supposed to keep up (or that he was supposed to wait up) was liberating.

    I let go of comparison.

    I let go of self-flagellation (at least about the hike).

    I let go of judgement.

    And I began to enjoy the hike.


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