When you were a child, chances are someone (or several someones) told you to look both ways before you crossed the road. Unfortunately, as we age, many people forget that sage advice. Instead, we tend to look one direction, at one perspective, and think that is the full picture . . . and then we are surprised when something comes barreling at us from a direction we didn’t even consider. 

Leaders always need to look both ways.

We will never get the full picture by only looking in one direction. Even when that direction seems like the “logical” perspective . . . when it feels absolutely “true” . . . when we have “proof” . . . when we can see it with our own eyes and therefore believe it has to be right. One sided solutions leave us vulnerable to unexpected risks that we didn’t even consider because, well, we “knew” we were right. Except, maybe “right” depends on which direction you are looking.

Always look both ways.

No matter how confident you are in the perspective that is driving your decisions, take a few moments to ask how someone might view the situation differently. If someone had a different life experience, if they were sitting in a different chair than you are, if they were looking in the exact opposite direction from where you are gazing . . . what might their perspective be? Could a good, smart, well-intended individual be just as convinced that they are right and your perspective is “wrong”? 

The space between the black and white of looking in one direction or the other is the sea of gray where much of leadership takes place. Because more often than not, leadership is not about right or wrong. It is about considering a range of perspectives and priorities and taking the next best step given the numerous variables that are “true.” And that doesn’t necessarily make the person who sees things differently bad or wrong. In most cases, it means that your priorities are not the same as theirs. If you take the time to understand their perspective, you might even find a way to address multiple priorities with a single solution.

But first, you have to look both ways.

And that can frustrate people who only want to you to look in one direction. Such people can accuse you of not being committed to “what is right”, of somehow waffling because you are seeking to understand a different perspective. Seeking to understand is not waffling, and decisions don’t have to be either/or. Sometimes, the best decisions are both/and, and the best leaders recognize that their decision is one of a range of viable options.

All it takes is a willingness to look both ways.

I have a plaque hanging over my desk that reads, “Courage doesn’t always roar. Sometimes courage is the quiet voice at the end of the day saying, ‘I will try again tomorrow’.“

I have lost count of the number of times that sentiment has given me comfort at the end of a particularly challenging day. Sometimes, leadership is about two steps forward and one step back. It’s about continuing to push on the fly-wheel, even when you don’t see any progress, because you know it is cumulative efforts that get things rolling. It’s about persisting in putting one foot in front of the other, even when the path is covered in fog. Courageous is not usually the word we think of to describe ourselves in such situations, but maybe it should be….

How many opportunities are lost because we don’t have the perseverance, the courage, to push on through the difficulties, setbacks and disappointments? Or the courage to step out into the unknown, even though such a move could advance your mission? How many times is it dogged (courageous) determination, rather than singular pronouncements, that make the difference in achieving the win?

In some respects, roaring courage is “easier”. That courage we call on at a moment of crisis, or when we draw a line in the sand. Those moments when we have to act — when people look to us to roar — do take courage, but in many cases, the situation is forcing our hand. Not so with quiet courage. Quiet courage is about making the hard decisions even when it is likely that no one will notice. Quiet courage is about continuing through the challenges in your pursuit of a goal because it is too important to stop short. Quiet courage comes from that small, still voice inside that won’t settle for less. 

Most leaders will have to display roaring courage from time to time, but it is episodic. You make a roaringly courageous decision, and then do your best to get back to business as usual as soon as possible. Quiet courage is more of a characteristic, it’s how you approach your leadership responsibilities — or at least try to — day in and day out.

Quiet courage may be overlooked or mislabeled, but make no mistake, it is courage … 

 … After all, it’s not about the roar.

Opportunties can be fleeting. In some cases, you may have just a moment to respond to a given set of variables. If you don’t make the call, your chance to have an impact, build a relationship, or change a trajectory may pass you by, never to present itself again. All true. It is also true that you can’t respond to every opportunity before you, and some things you could respond to (and maybe would like to respond to) may actually be a distraction from reaching your strategic goals. How do you decide which opportunities to pursue and which to take a pass on? Trying viewing them through these four lenses.

Is it the right thing to do?

Start with your values. This may take the form of a nudge from your gut . . . that inner voice that says “you have the skills to positively impact this situation.” Please note, the right thing is often not the easy thing, which increases the chance that you will pass on the opportunity. A bit of extra effort to live out your values is worth the investment, every time.

Does it align with your strategic goals?

One of the challenges for many leaders is that there are a lot of things you could do . . . and could do well. Could is not the same as should. Could lives in the land of distractions. It is the shiny object that draws your attention away from the end goal you have intentionally identified. Always ask how an opportunity furthers your goals. If it doesn’t, it’s a distraction.

Is it a value-add or just a fad?

“Everyone else is doing it” is not a compelling reason to invest your time and energy into an activity dressed as an opportunity. How does pursuing a potential activity further your goals? Sometimes passing on an “opportunity bandwagon” that everyone else is jumping on means that you will have the capacity to pursue another unique option that really does move the dial and distinguishes you from the crowd.

What will you have to say no to?

Every yes comes with an often invisible set of no’s. If you invest your time and energy into one opportunity, that means you won’t have have time for/are saying no to one or more other opportunities. Even if something is consistent with your values, aligns with your goals and adds value to your efforts, a final consideration should be what will you have to stop doing to start pursuing this opportunity. What may seem like a good idea when viewed in isolation may not be the top priority when considered in the context of what you would have to give up.

Opportunities abound. So do distractions . . . and they may look a lot alike on first glance. The clearer your vision, the easier it is to see the difference.

I recently had a chance to be a part of the studio audience for a podcast interview with Stephanie Chung, Chief Growth Officer for Wheels Up, and former President of JetSuite. One of the questions the interviewer asked was something along the lines of, “Now that you have broken through so many barriers as a woman, and woman of color, to reach the highest levels in your organizations, has it gotten easier?” Her response struck a chord. She looked the interviewer right in the eye and simply responded, “different level, different devil.”

It is so easy to lure ourselves into to thinking, “when (so and so) happens, this will get easier.” When I get the next promotion . . . when the kids get back in school . . . when I finish this project . . . This kind of passive, victim thinking will only lead to frustration on everyone’s part. Maybe it is not supposed to get easier. Maybe we are supposed to get better. At prioritizing, at  being selective in what we commit to, and learning to say no to someone else’s worthy project so we can say yes to our own.

Different levels also require a different lens. As you “move up” in an organization, you will likely be moving from near-term project-specific tasks to long-term strategic initiatives . . . different devil indeed. No longer able to check most items off your do-do list as completed, the strategic approach means days where you have no idea if you actually made progress or not (and you know what the devil will be whispering in your ear). It is dealing with a myriad of opinions, and laying ground work that may take months or even years to come to fruition. It is encountering “pull your hair out” frustration and set-backs that few if anyone is even aware of, and yet that command large portions of your time.

With the right attitude, however, you can call the devil’s bluff. Because each successive level gives you the opportunity to expand your impact, to shape the future of your organization in ways that would not have been possible if you hadn’t chosen to look the devil in the eye and say, “step aside, I’ve got this.” As you move from one level in your organization to the next, things will not get easier. You just get better. You learn new skills, grow a thicker skin, and develop the relationships and connections that can help you, and your organization thrive.

Different level, different devil? You bet. So stare that devil in the eye and keep moving. You’ve got big things to accomplish.

Many of us have this picture of a successful leader as someone who is confident and decisive. The problem with that view of leadership is this: When we as leaders feel less than confident regarding the best path forward we may start to doubt our ability to lead . . . yet our willingness to question our own thinking may actually be a sign of superior leadership. Which might prompt one to ask, “Is confidence over-rated?”

In Good to Great, Jim Collins notes a Level 5 Leader demonstrates personal humility and professional will. Blair Shepherd from PwC identifies one of the six paradoxes of leadership as the “humble hero”. And, there is a growing body of research on the importance of intellectual humility in innovative problem solving — a key aspect of effective leadership.

Okay, so it would seem that humility is a good thing. Is confidence the opposite of humility . . . thereby making it a bad thing? Actually, arrogance is the opposite of humility, and arrogance does negatively impact your ability to lead. Arrogance is an exaggerated sense of superiority — “I’m the leader, therefore my ideas are the best ideas.” True confidence comes not from thinking you have all the answers, but from a recognition of your skills and abilities — “I may not know the answer right now, but I have the tools to figure it out.” Humility is a recognition of the strengths of others as well as the limits of one’s own importance — “By listening to and learning from others, we can arrive at the best solution. It’s not all about me.”

Arrogance shouts, humility listens, confidence deliberates.

Confidence isn’t over-rated, but it is often ill-defined. Confidence is not about having all the answers. (Whew!) It is about knowing you have the ability to figure things out. Confidence brings calm. It encourages curiosity. It considers options. It steps forward courageously, and recalibrates when necessary. Confidence is also contagious. When a leader demonstrates it, followers gain it. As noted above, true confidence is often laced with humility — “It’s not about me, but it is up to me.” 

Feeling less than confident? Remember, just because you don’t have the answer right now doesn’t mean that you don’t have the ability to find a solution. Decide that you’re going to get there, take a deep breath, seek input from others, and then take a step. It’s the best way to get to the other side. Of that, I am confident.

Trust seems to be in short supply these days. And a lack of trust costs all of us . . . in terms of time, resources, and overall progress on our missions. The challenge for a leader is that you can’t “make” someone trust you. You have to earn it. Not only that, in our current environment, for a host of reasons, there is a tendency for people to assume ill-intent — to assume that leaders aren’t trustworthy until you “prove” them wrong. So how do you do that?

1. Stay off the ladder.

I have written before about ladders of inference. It is the tendency we all have to select specific data to focus on, to add meaning to the data we select, make assumptions based on the meaning we have added, draw conclusions based on that added meaning, which affects our beliefs, which influence our actions . . . all in the blink of an eye, often without us even being aware of it. Social media pushes us higher up the ladder by feeding us even more information to “support” the assumptions and beliefs we bring to the table. And you aren’t the only one climbing that ladder. The people you would hope trust your leadership have their own ladders too. How do you stop the climb? Curiosity. Ask others for their perspective. Listen to their response. Assumptions undermine trust and make progress harder. Stay off the ladder.

2. Tell them why.

One good way to keep people off the ladder in the first place is to tell them why you are taking certain actions. You don’t have to give them every last detail or share confidential information, but if you help them understand your intent they are much less likely to make assumptions about what is driving your actions. By sharing the thinking behind decisions, you are offering your trust to your people. And when you take the first step in the dance of trust, it is easier for others to follow suit. Not only that, but when your people know the reasons behind your decisions, they have the chance to offer insight that just might get you to your goal faster and more effectively.

3. Remember, it’s not about “them”.

A recent article in Inc. magazine suggested that the way to stop passive aggressive behavior and strengthen relationships is to attack the problem, not the person. Good advice indeed. When we start to see people as the problem (or they see you as such), then all of a person’s actions become suspect. What if, instead, you as the leader take the responsibility to identify the problem at hand. You may not appreciate the person’s behavior, but responding to that in the moment, rather than the actual issue, only results in the creation of another problem. When you model focusing on the problem rather than the person, you make it safe for others to do likewise, which creates a healthier, more trusting work environment for everyone.

Want to bring out the best in your people, and propel your mission forward? A good place to start is by earning their trust.

At the risk of causing shudders among many a leader and consultant, I am not a big believer in strategic plans. In our organization, we use a strategic framework. That might sound like semantics to some, but I don’t see it that way and here is why: One dictates step-by-step actions (how), the other guides decision-making in a specific direction (where). And in today’s fluid, fast-changing environments, pre-ordained actions (how) may be rendered outdated, inappropriate or impossible before the ink is even dry on the plan — regardless of how long one spent creating it in the first place.

Dwight Eisenhower once noted that, “In preparing for battle, I have always found plans are useless but planning is indispensable.” I couldn’t agree more. I am a huge proponent of the strategic planning process, just not the definitive plans that often result. Why? Because over-reliance on a specific process can leave those charged with carrying it out unclear on how to proceed when things don’t go according to the plan . . . and things rarely go exactly according to the plan. (What is that saying . . . Man plans and God laughs?)

Is it critical to know the end goal? Absolutely. Is it helpful to have considered a range of possible scenarios? Yep. Is it important to understand the organization’s priorities? Most definitely. In my experience, however, organizations act their way forward rather than plan their way forward. Individuals within the organization make moment-by-moment decisions regarding the path, the actions, that have the greatest likelihood of moving the organization toward the clearly identified end goal. How can one know two years out, or sometimes even two months out, the best decision given a myriad of ever-changing external variables? And yet, if a specific set of expected actions is outlined in an approved multi-year strategic plan (presumably to which staff are being held accountable), how many people will follow the plan rather than exercising their good judgment?

It is not about the plan. It is about understanding what the organization is trying to accomplish, the assets it brings to the table, the barriers it is likely to encounter, and staff members who have both the context and competencies to make decisions that move the organization closer to its ultimate goal. Smart, well-informed leaders monitoring the situation and making adjustments in the moment will do far more to help an organization succeed than the best thinking from a year ago.

Strategic success is about preparation and priorities. It is not about the plan.

I was in a training with a group of nonprofit leaders yesterday, and while I would like to think the content was relevant and helpful, equally important was how the time together fostered a sense of community among a group individuals facing many of the same challenges and opportunities. Leadership can be a lonely thing . . . perhaps now more than ever with our increasingly digital/zoom/remote workplaces, and often only a handful of people who understand first-hand the unique pressures of your role. How does a leader sustain his or her passion, commitment and can-do spirit? By actively cultivating communities of support. Yes, communities — plural — because a leader needs different kinds of support at different times. What should those communities look like? They can be as individual as the leader, but here are some good suggestions to consider:

A professional community. 

Especially if you don’t have someone in a peer role in your organization, it is important to find people in similar roles that you can bounce ideas off of, ask for honest feedback, and occasionally commiserate with a bit. I have found professional industry associations are a great way to connect with such people. Peer leaders in a similar industry can offer you a relevant perspective without you having to explain the backstory or variables. Chances are they have been there and done that, and there is great comfort in knowing that others are experiencing similar challenges and opportunities.    

People who have known you a long time.

Lifelong friends can keep you grounded like no one else. They aren’t impressed with your title or professional accomplishments – they know far too many embarrassing stories and aren’t afraid to remind you about them.  No matter how you advance in your career, long-time friends are a great way to make sure you don’t lose sight of your core values and what is important in life (and, contrary to what you might hear at work, it probably isn’t you.) These can be family members, high-school friends, people you grew up going to church with . . . people who knew you before you were someone people wanted to know. 

Friends who make you laugh.

The vast majority of people just don’t laugh enough. Laughter puts even the biggest challenges in perspective and yet, when we are stressed out it tends to be one of the last things we think about doing. So pre-emptively schedule regular time with a group of friends who make you laugh. Even once every few months can have a huge positive impact on your outlook. When you need it the most, scheduling time with this important group probably won’t occur to you. Plan ahead so the stress can leak out amid the laughter.

What other communities of people help you through the challenges of leadership? The role can at times feel lonely, but you don’t have to. It’s just a matter of finding your communities.

I was on a webinar this morning and heard a phrase/description that I hadn’t heard before but that immediately resonated with me — the 10-way tie. That’s when a leader looks at his or her to-do list to try to prioritize tasks . . . and it’s a 10-way tie. Everything is critical. Everything is urgent. And there is no way all 10 things can take priority. Not only that, but if you try to do all 10, you won’t do any of them well. What’s a leader to do? A few things to consider:

1. Whose priority is it?

People will often try to make their priority your priority. That is not to say the project is not important, however ask yourself who is driving your sense of urgency? If someone didn’t get you a document until the 11^th hour and then expects you to drop everything to meet a deadline, that is unrealistic. What you have is a crisis of someone else’s making, based on someone else’s priorities. In such cases, it is absolutely appropriate to push back and communicate the amount of time it will reasonably take to complete the project. You might be surprised at how often the person 1) didn’t think about the impact on your schedule and 2) actually could allow you a bit more time. When the timeline is firm, ask about what other projects could be de-prioritized, or what additional resources are available to support completion of the project. 

2. Which items align most closely with your strategic goals?

Prioritizing based on strategic goals doesn’t mean that, on the surface, other items on the list may not appear more urgent in the moment. The urgent vs. important dilemma is real, and occasionally the urgent has to take precedent. Notice I said occasionally. Addressing the urgent first can also become a habit. Let’s face it. It can feel good to resolve an urgent matter (which screams louder). We can also usually check those things off the list, which feels productive when so many strategic efforts don’t have easily check-offable tasks. Prioritize those things tied to your strategic goals.

3. Is it a priority, or do you just really like to do it?

We all have a tendency to weigh more heavily in importance those things we really like to do. We excel at them. They tend to energize us and make our day go better. All of which are good things . . . unless they get in the way of what is objectively a higher priority. Often these are recurring tasks, but they remain on the list because it is so easy for us to extol their virtues. A good way to combat this is to ask someone, who is aware of the organization’s strategic goals, how they would prioritize your list. If the same item sinks to the bottom of how someone else would prioritize your list . . . especially if this happens more than once . . . chances are it is something you like to do. Again, not bad, just maybe not the top priority.

If everything is a priority, nothing is. You’re the leader. It is up to you to break the 10-way tie.