"Leadership isn't always rewarding. It can feel like a bottomless pit of problem solving and adult-sitting. Leadership is exhausting, repetitive, and requires a constant stretch of your emotional and intellectual skills. It demands an 'always on' mentality, as you're expected to have all the right answers and make all the right decisions, often on the fly. But it doesn't mean leadership isn't important; on the contrary, often the things we struggle with yield the biggest return. It's okay if you admit that leadership can be hard and unenjoyable, because the benefits of being successful at it can be life-changing."
Leadership isn’t always rewarding.
It can feel like a bottomless pit of problem solving and adult-sitting. Leadership is exhausting, repetitive, and requires a constant stretch of your emotional and intellectual skills. It demands an “always on” mentality, as you’re expected to have all the right answers and make all the right decisions, often on the fly. But it doesn’t mean leadership isn’t important; on the contrary, often the things we struggle with most yield the biggest return. It’s okay if you admit that leadership can be hard and unenjoyable because the benefits of being successful at it can be life-changing.
PART ONE – LEAD YOURSELF
Challenge 1: Demonstrate Humility
Has your lack of humility ever limited your perspective or lessened your influence as a leader? Would you even know if it had?
Leaders who fail to demonstrate humility often find themselves leaning toward arrogance and seeking outside validation. They rarely listen to anyone but themselves, and thus miss opportunities to learn and course-correct. They often turn conversations into a competition and feel the need to “one-up” others and have the final say.
In Get Better: 15 Proven Practices to Building Effective Relationships at Work, Todd Davis writes:
“Those who are humble have a secure sense of self—their validation doesn’t come from something external, but is based on their true nature. To be humble means to shed one’s ego, because the authentic self is much greater than looking good, needing to have all the answers, or being recognized by one’s peers. As a result, those who have cultivated humility as an attribute have far greater energy to devote to others. They go from being consumed with themselves (an inner focus) to looking for ways to contribute and help others (an outer focus). Humility is the key to building solid character and strong, meaningful connections.”
“Often the things we struggle with most yield the biggest return. It’s okay if you admit that leadership can be hard and unenjoyable because the benefits of being successful at it can be life-changing.”
Challenge 2: Think Abundantly
Where is scarcity in your thinking impeding the best results? How difficult is it for you to share credit, praise, recognition, or power?
Thinking abundantly is essentially the difference between a scarcity mentality (get yours before it’s gone) and an abundance mentality (there’s plenty to go around for everyone). A colleague shared this advice: “You’ll never have enough until you define how much is enough.” Define “enough,” or you’ll be constantly worried you don’t have it.
Make a conscious effort to publicly praise anyone who truly warrants it, and share credit freely. Applying the principle of abundance, you can become a more gracious, generous, and respectful leader. You won’t miss out by recognizing the accomplishments of others.
Challenge 3: Listen First
When was the last time you listened to understand rather than to reply?
Listening often requires a generous gift of time and attention to forget about your own needs and focus intently on someone else’s. To really listen requires discipline, self-control, and a genuine desire to understand the other person’s point of view. Listening requires you to care, perhaps even more than you may want.
When someone else is talking, purposely close your mouth and focus on the physical sensation of your lips being pressed together.
When the other person has paused, count to seven before responding. Doing so will increase the likelihood that they’ll continue, often sharing crucial details about their point of view or situation.
It can be freeing to put yourself aside and focus on someone else. Spending time in that quiet place of connection with someone else in their angst, their joy, or their frustration can create bonds that last a lifetime.
Challenge 4: Declare Your Intent
Have you ever had incorrect intent ascribed to your actions? Why did that happen?
Many think of leadership as a war of political gamesmanship and cutthroat advancement. Such outdated Machiavellian attitudes have evolved into the desire to build cultures of high transparency, collaboration, and trust. Today, few people want to work in environments of concealment and one-upmanship. Declaring our intent in conversations, especially in adversarial or high-stakes conversations, is crucial to creating mutual understanding, if not mutual agreement.
Make sure that what you intend people to hear and see is what they actually hear and see. The less clear you are, the more you are responsible for their lack of clarity.
Challenge 5: Make and Keep Commitments
Are you damaging your credibility through too many unfulfilled commitments? Are you a serial overcommitter?
Everyone’s bandwidth is different in terms of their capacity to take on and execute their commitments with excellence. If you find yourself in the mess of overcommitting and underdelivering, consider exercising uncharacteristic restraint the next time you’re approached by a colleague, friend, or family member. They may be unwittingly attempting to move you past your breaking point.
Our capacity to do is always more than our capacity to do with excellence. No reasonable person can resist a response like: “I truly would love to be a part of that, but I’m so cognizant of not wanting to disappoint you and others I’ve already committed to that I’ll have to decline. If something changes with my current level of commitments, I’ll surely reach out to you. Thank you so much for your trust in me.” The shorthand version of this is, “Let me get back to you on that.”
Many leaders love to say yes. But we need to love no much more.
“Our capacity to do is always more than our capacity to do with excellence.”
Challenge 6: Carry Your Own Weather
How would your team describe your leadership style when things are stormy? How about when things are calm?
Leaders who carry their own weather exercise emotional discipline and resist the temptation to allow external dramas to distract them. When we’re triggered emotionally, it’s easy to forget we have a choice as to how we will respond. Central to Habit 1: Be Proactive® from The 7 Habits is the concept that between what happens to us and how we react exists a space. In that space lies our freedom and power to choose our response. We all experience situations where it’s tempting to react quickly and without thought. This is where the choice of carrying your own weather manifests itself.
To carry your own weather:
- Define your personal and professional values (from which your behaviors will be exhibited in both good and rough weather).
- When faced with a situation that threatens to hijack your emotions, think carefully about the response you won’t have to apologize for and that leaves people whole.
- Recognize that most flash responses won’t represent how you feel an hour (let alone a day) later. Consider saying: “Could I have a few hours to think about my position so that it is congruent with what I am going to think and feel later on?”
Remember that you are your own meteorologist. If you don’t like the weather, change your response to it.
Challenge 7: Inspire Trust
Think of a person who had confidence in you and extended trust. Reflect on its ongoing impact. Will you have the same impact on your team members?
Trust is one of the most written and talked about topics in the business world today. Ask yourself, “Am I more inclined to trust or distrust others?” Is your natural tendency to be suspicious of others, or are you able to extend trust even to those who have not yet fully earned it?
Success is often the direct result of someone extending trust and allowing individuals to learn a critical leadership trait. Great leaders extend trust, sometimes beyond even what is deserved.
Challenge 8: Model Work/Life Balance
If paparazzi had followed you last week, would they have seen a balance of activities at work and outside of work? What’s the impact?
It’s well understood that, while we talk about balancing work and private life, if you really want to succeed as a leader, you clock as many hours as you can, life balance be damned.
Without the energizing and renewing activities that take place outside the office, you can’t be whole or fulfilled. If you’re not fulfilled in multiple areas of your life, you won’t be as productive at work. When leaders don’t have a life, they not only look pitiful in the eyes of their teams, they also set a very low standard for how others behave, consciously or unconsciously. What you model is what you will see come to life in your colleagues. They will draw conclusions about what is acceptable and what is not, based both on what you say and what you do.
PART TWO – LEAD OTHERS
Challenge 9: Place the Right People in the Right Roles
How many people on your team are in the right role? Do you need to make adjustments?
Building a winning team can be one of your greatest legacies as a leader, but it’s rarely recognized or rewarded in real time. In fact, you’ll likely only get credit for it after the team disbands or you’ve moved on.
To accelerate the process of getting the right person into the right role, carefully consider these questions:
- What skills and passions does this person have, and what type of team can make the most of them?
- What culture will this person experience in their new role? Are they nimble enough to assimilate into a strong culture, or are they influential enough to lead a better culture?
- Which changes could you make in your own style to better ensure their success and impact in their new role?
Successful leaders often discover they’re much like the eHarmony of business—they embrace the art of matchmaking and introducing the right people to the right roles. Many will have to fail their way to eventual success—the key is how fast can you get there with as few divorces as possible.
Challenge 10: Make Time for Relationships
Do you practice the principle that, with people, slow is fast and fast is slow?
Real relationships require us to slow down, even when everything around us is demanding we go faster. Our effectiveness as leaders requires us to take the time to get it right.
Challenge 11: Check Your Paradigms
Are you seeing people and situations accurately?
Leading difficult conversations is a leadership challenge that’s so daunting many avoid it. Yet, if you don’t do it as a leader, you frankly don’t deserve your job. These conversations are not something you can neglect, even if you’re convinced you can work around them or they’re not that important, given your long to-do list.
You have to practice, role-play, and rehearse these conversations repeatedly. Unlike the countless other leaders who are well-intentioned but never exercise the courage to be honest, you can change the entire trajectory of someone’s life.
Successful leaders can learn to lead difficult conversations from colleagues who are senior, peers, other team members, and specialists. Sit down and share the situation with someone at the right organizational level and ask how they’d handle the conversation.
“Building a winning team can be one of your greatest legacies as a leader, but it’s rarely recognized or rewarded in real time.”
Challenge 13: Talk Straight
When was the last time you technically told the truth, but left a misleading impression?
Not every culture values straight talk. As a leader, it’s your judgment to understand your latitude. Straight talk can be delivered in respectful and honorable ways without ever diminishing someone’s reputation. The opposite of straight talk includes posturing, positioning, spinning, or technically telling the truth but leaving the wrong impression. Our ability to talk straight comes down to using clear, accurate, and simple language to ensure that what is said is what is heard and, perhaps most important, what is being heard is being understood.
Leaders who talk straight:
- Call things by their right names using common, plain language.
- Tell the truth in diplomatic yet clear language.
- Don’t try to sound more intelligent than they are.
Leaders who talk straight leave their listeners clear about the intended message because there was nothing added to distract or confuse. They don’t leave room for misinterpretation or guessing. They stay as far from spin as possible.
Challenge 14: Balance Courage and Consideration
Do your wins come at the expense of others? Or do you allow others to win at your expense?
The best leaders assess their balance of courage and consideration intentionally and repeatedly. Courage often means telling it like it is, calling things out, stepping up to difficult conversations, and addressing tough issues. It also sometimes means saying nothing. When overdone, it can take the form of bullying, being overly brash and undiplomatic, or lacking empathy. Consideration often means showing kindness, being polite, and assuming the best in others. Too much consideration can become avoidance, capitulation, neglect, and disenfranchisement. Most of us have a natural tendency to one or the other.
Every culture has its own equilibrium. Some value brasher, more outspoken styles, while others prefer a hold-your-tongue approach to avoid conflict. How do leaders find this balance while accommodating the diverse needs, preferences, and traits of their team members? By demonstrating courage in sharing opinions, tactfully calling out mistakes (including our own), and diplomatically challenging one’s direction while simultaneously accounting for people’s feelings, insecurities, and cultural norms. Geographical and organizational cultures do affect the courage/consideration balance, but principled leaders can thrive anywhere because most people want to hear truth when it’s respectfully presented.
Challenge 15: Show Loyalty
When was the last time you gossiped or disparaged someone behind their back?
Dr. Covey said, “When you defend those who are absent, you retain the trust of those present.” To show loyalty:
- When someone is absent, speak about them as if they were standing beside you. Visualizing the person being present will dramatically change how you talk about them.
- Assume your email will be forwarded to the person you’re writing about. When composing an email about another person, write as if you know the person will eventually read it. Also, the use of “bcc:” is cowardly and disloyal, and something to avoid nearly all of the time.
- Assume good intent. Human beings are often conditioned to assume others have bad intentions. Stop and reflect on someone’s actions with the assumption they had good intentions.
Once the value of loyalty permeates your company culture, you’ll wonder how you ever functioned without it.
“Exercise the courage to be honest, you can change the entire trajectory of someone’s life.”
Challenge 16: Make it Safe to Tell the Truth
Are your people as forthcoming with bad news and negative feedback as they are with good news and positive feedback?
The higher up you get in an organization, the more insulated you are from the truth. The phrase make it safe to tell the truth is talking about you, the leader, owning the responsibility to make it safe for others to be truthful. To help make it safe for others to be truthful in your presence:
- Show sincerity in wanting to know their truth. (I say “their” because not everyone’s version is accurate, complete, or helpful.)
- Build their confidence that there is zero downside to speaking up (no retribution, punishment, or risk).
- Prove through continued experience that you won’t dispute or challenge their position, defend your behavior, or dismiss their feedback out of hand. Perhaps most important, show through your new behavior that you value their risk-taking enough to improve.
“The higher up you get in an organization, the more insulated you are from the truth.”
Challenge 17: Right Wrongs
When you break a promise, is your first instinct to defend yourself, rationalize, minimize, or ignore it altogether?
A colleague and mentor introduced an empowering concept termed “pre-forgiveness.” Essentially, it means: You’re pre-forgiven. You will make mistakes. It’s part of each of our journeys. If we live in fear of making a misstep, we won’t place any bets, take any risks, or stretch our skills. This doesn’t mean people get a free pass for bad behavior, but rather you acknowledge that everyone falls short, and it’s okay.
When righting wrongs, it’s remarkably disarming to take full responsibility. Nothing neutralizes anger more than a sincere, excuse-free apology and an action to correct the situation. Consider some version of the following when you find yourself having wronged someone:
“I want to tell you something very important. I’m truly sorry for the way I behaved. I was wrong. I own it. I’m sorry. I hope you can forgive me, and I intend to make a sincere effort to ensure I don’t ever do that to you again or to anyone else. I have learned a hard and valuable lesson sadly at your expense, and I want you to know how seriously I am taking it. Furthermore, I intend to take [fill in the blank] action to make it right between us. Is that something you would value, or do you have a better suggestion I should consider?”
Challenge 18: Coach Continuously
Do you see every interaction with team members as an opportunity to build confidence and develop potential?
Coaching is imperfect and often messy, but also real, relevant, and replicable. Coaching continuously requires a lot of engagement. First, you have to inherently want to lift others up, not just by affirming what they’re doing right, but also by addressing what’s wrong, slightly off, or even unacceptable. It takes a mindset shift, courage, diplomacy, practice, and repetition. Consider these best practices:
- Have a “check in” versus a “check on” process.
- Recognize the different ways team members want and need coaching.
- Ensure that everyone has the resources and tools to complete their work and help others.
- Add coaching to your daily task list.
Challenge 19: Protect Your Team Against Urgencies
How will you find the courage to keep your team focused on what is most important, including saying no to some of your own best ideas?
If you’re a corporate adrenaline junkie, urgencies can be a tempting distraction. They can bring instant validation and gratification. The adrenaline high from urgency is invigorating. For a time, anyway. Then it peaks and quickly fatigues people.
As leaders it’s our responsibility to help protect our teams against urgencies by identifying and rewarding the specific behaviors that lead to achieving our goals. Focus your team members on the wildly important efforts and not the wildfires—even the ones you set! But first, ensure you haven’t modeled or reinforced a culture that rewards firefighting more than fire prevention.
“Ensure you haven’t modeled or reinforced a culture that rewards firefighting more than fire prevention.”
Challenge 20: Hold Regular 1-on-1s
What’s preventing you from holding 1-on-1s with each of your team members?
Nothing is more important than the people you lead. What they need from you is time. They need 1-on-1s so they can bring up issues hindering their progress, get feedback and coaching, create a development plan, and problem-solve with you. 1-on-1 meetings are one of your most important tools for increasing your team’s engagement.
Be realistic about how often you can hold regular 1-on-1s. Don’t announce you’ll hold weekly 1-on-1s and then cancel them. This is an issue of quality over quantity, especially when the firehouse siren goes off. Start slow by gathering your team together and declaring your intent.
Remember it’s your associate’s meeting, not yours. You should do 30 percent of the talking compared to their 70 percent. Don’t confuse this with your regularly scheduled team or staff meeting where the agenda can typically be all yours.
“Nothing is more important than the people you lead. What they need from you is time.”
Challenge 21: Allow Others to be Smart
Do you need to be the smartest person in the room?
In Liz Wiseman’s book, Multipliers: How the Best Leaders Make Everyone Smarter, she invites leaders to assess several key questions: Are you the genius or the genius maker? Are you a Multiplier (someone who uses their intelligence to bring out the best in others) or a Diminisher (the “smartest person in the room” who shuts everyone else down)?
Leaders who struggle with allowing others to be smart are often driven by their ego, insecurities, or a desire to jump in and top any idea. Here are three skills you can use to empower and engage others to showcase their creativity, experience, and perspectives:
- Consider the percentage of time you spend talking versus listening.
- Decide when to be the expert with the “right” answer, and when to allow your team to work through the process of coming up with it themselves.
- Step back from being the driver of the discussion and ask someone on your team to take the lead.
PART 3 – GET RESULTS
Challenge 22: Create Vision
Have you articulated an inspiring vision so your people choose to volunteer their best?
Creating a vision means defining where your team is going and how they will get there. It’s not unusual for a leader, after a grand pronouncement, to sit back and assume their vision will happen. In truth, many bold strategies never reach liftoff because team members were either confused, uninspired, or had a “this too shall pass” attitude.
Consider these best practices for creating and communicating a vision:
- Adapt your message to the culture.
- Articulate and repeat the vision at every appropriate opportunity.
- Create ambassadors.
No leader has ever overcommunicated an inspiring vision. Worthy aspirational projects and initiatives typically fail because leadership wrongly thought they had been sufficiently translated throughout the team or organization. Or in some cases, they lost interest themselves.
Challenge 23: Identify the Wildly Important Goals (WIG)
Does everyone know the team’s top two or three priorities (WIGs) and how they will align their efforts to achieve them?
Wildly Important Goals (or WIGs) are the few, highly important goals that must be achieved or no other goal matters. Despite their critical importance, WIGs can be neglected because of the temptation to focus on the urgencies of the day. To identify the WIGs for your team ask, “If every other area of our operation remained at its current level of performance, what is the one area where change would have the greatest impact?” Then share them with your team for input and consensus.
Challenge 24: Align Actions With the Wildly Important Goals
Are the efforts of your team members moving your goals forward? How can you make it easier for them to do so?
If a goal is elevated to WIG status, it’s vital to the team’s and the organization’s survival or growth. That also means every goal your team is trying to realize can’t be a WIG, as that dilutes the significance and commitment to marshal a heightened level of focus, time, resources and attention.
Meaningful change comes from the inside out. It has to start with you as the leader, committing to and then enacting new behaviors. When you change your behavior, others will see your commitment to accomplishing the WIG. Remember to choose a change in behavior that’s at the same level you want to see in your team members, unless your role is more removed or narrowly defined. A Chief Marketing Officer is likely to engage with a WIG at a very different level than a Digital Content Manager or Social Media Director. The commonality is new and better behaviors on display for all to see.
Leaders who successfully align their actions to their WIGs do more than trumpet a new motivational kick-off—they make fundamental shifts in how they plan their weeks and days and how they staff and use resources.
Challenge 25: Ensure Your Systems Support Your Mission
Effective leaders create systems that make it easier to achieve results. When was the last time you did a “systems check”?
As leaders we tend to settle into acceptable patterns, especially around areas of the business that seem fine. We often step back and allow systems to just do their thing, even when they’re not perfectly aligned to our mission and goals.
Think about this in terms of your own team—do your systems support your mission? Have you engaged the patience and due diligence to understand how your systems align or misalign to your strategies, your WIGs, and your client needs? How about your employees’ needs?
Consider the following systems-alignment questions:
- Are the right people with the right skills doing the right work?
- Are the right roles and responsibilities in place for people to work well together?
- Are people recognized and rewarded in the right way?
- Are the right resources available to succeed?
- Are the right decisions being made by the people closest to the work?
- Do we have the right processes in place to get the most important work done?
While you likely don’t have direct control over all the systems and processes you’re working with, mindlessly accepting them as the status quo won’t do. Your job is to understand the rationale for and nuances of any system that feels misaligned to your mission and goals, and influence (or, if you have the authority, make) improvements.
“Equating “busy” with “productive” has been debunked in all but the most antiquated of cultures.”
Challenge 26: Deliver Results
Are you and your team delivering activities instead of results? Are the results the right ones?
If you’re a leader, you already have a reputation for driving results. The question is, what kind of reputation? One common mistake is for leaders to confuse activity with results. Equating “busy” with “productive” has been debunked in all but the most antiquated of cultures.
Delivering results requires leaders to reject the belief that activity equals results; to affirm that, they deliver the right results by aligning their work to the mission and goals of the organization. Such leaders lead their teams with care and consideration so they achieve results in the right way while being mindful of the health and welfare of their teams.
Challenge 27: Celebrate Wins
Do you spend as much time celebrating the achievement of goals as you do setting them?
People like to win—but not “fake” win. Your team wants to work for it. But they don’t want the finish line moved, and they don’t want to kill themselves in the process.
Budget should never constrain your ability to celebrate wins. People might be happy to get some free food or gifts out of a celebratory event, but if you invest time into recognizing them, you can make a bigger, more lasting impression. Spend an hour the night before and generate a list of each person’s unique contributions to a big win. The next day, go one by one around the room and share.
Challenge 28: Make High-Value Decisions
Do you dedicate your time to the activities that will yield the most impactful results on the organization and your team’s mission?
As a leader, your reputation is, in essence, the sum of your collective decisions. Basically, you’re paid to decide—it’s that simple.
High-value decisions result in the actions that bring disproportionate progress toward the organization’s mission, vision, and WIGs. Assess how you spend your time by asking yourself, “Is what I am doing now, or what I am going to do next, progressing our mission and vision or our Wildly Important Goals?”
Best practices for high-value decision making include:
- Focus. With unlimited choices comes the temptation to take on those that don’t meet the high-value criteria.
- Don’t go it alone. If you’re stuck, feeling disenfranchised, or just can’t decide between two compelling but incompatible choices, get help.
- Don’t go for the easy wins. As leaders, we may be tempted to play to our strengths, find the path of least resistance, and go for the easy wins that will bring recognition and reward. But rarely is that the path that leads to high-value decisions.
Challenge 29: Lead Through Change
When leading change, are you calm, confident, and focused—or anxious, threatened, and scattered?
Change comes at us nonstop in every form: organizational structures, market competition, government regulations, tax laws, revenue expectations, financial and accounting requirements, quality initiatives, unexpected events…it’s unrelenting.
The emotional impact organizational change has on your team must not be underestimated. Consider these practices useful for leading through change:
- Recognize how the change impacts you. How you relate to and experience it will impact how you communicate it to others.
- Identify the level of transparency. Be intentional about what you disclose to ensure your team can process the change at the speed they need to.
- Decide what your communication style will be during the change. You may need to balance your own mixed feelings while honoring your professional responsibility.
Challenge 30: Get Better
Are you consistently assessing your relevance and advancing your skills and capabilities?
This challenge isn’t about making incremental improvements in your professional development, relevance, or competencies. It’s about not just doubling down but quadrupling down in order to stand out and write your future. The best tactical advice for getting better comes from The Speed of Trust:
- Commit to continuous improvement.
- Increase your capabilities.
- Be a constant learner.
- Develop feedback systems.
- Act upon the feedback you receive.
A Final Thought: What About Character?
There is one foundational challenge, more critical than anything else, not included here: character. None of these leadership challenges matter if you fail on the character challenge.