Graybeard Leadership and Executive Coaching
Helping leaders grow since 2014
New Supervisor Survival Guide - Table of Contents
Shift to Developing Great Individual Contributors
The Dozen Key Skills
Get Off Autopilot
The Dozen Key Skills
Skill 1: Listen To Understand
Skill 2: Ask Questions that Encourage Thoughtful Discussion
Skill 3: Provide Feedback that Encourages Thoughtful Action
Skill 4: Delegate Challenging Work
Skill 5: Establish Clear Accountability Standards
Skill 6: Overcome Fear of Tough Conversations
Skill 7: Encourage Innovation
Skill 8: Inspire Commitment
Skill 9: Articulate Your Authentic Leadership Style
Skill 10: Foster a Healthy Work Environment
Skill 11: Lead Former Peers
Skill 12: Imagine the Future
Begin Your Lifelong Leadership Journey
Foreword
Why should anyone under 40 care what an old, retired guy writes about leadership? To quote my friend Mike, another old, retired guy and former manager of a city with half a million citizens, "Us old guys, we know a few things.”
This book distills fifty years of observing good and bad leaders, making mistakes, reading books and articles, attending leadership development programs, training and working as an executive coach, leading teams ranging from six Boy Scouts to hundreds of peers, and serving as the Chief Financial Officer of a multi-billion-dollar organization.
I wish someone had given me this book when I became a new supervisor. My hope is that supervisors find it useful in speeding their leadership development journey and avoiding at least a few of the mistakes I made along the way.
This book is only possible due to lessons I’ve learned from partnering with great coaching clients. After several thousand hours of coaching conversations with hundreds of clients, one thing has become abundantly clear: from small, private, family-run businesses and start-ups to the largest corporations and government agencies, most leaders struggle with many of the same challenges. This Guide addresses the dozen most common challenges confronting new supervisors; additionally, it offers communication and leadership techniques, with accompanying self-observation and accountability suggestions, that have been implemented successfully by real people in real work settings.
They’ll work for you too.
Introduction
I met Matt for our first coaching conversation on his second day as the newly promoted supervisor of a team of ten analysts. Every day, hundreds of great individual contributors are promoted to supervisor or team leader and many, like Matt, experience conflicting emotions. They are very excited, a bit stressed, not entirely sure they want the extra responsibility, and slightly overwhelmed. Like most leaders, Matt had earned his promotion because he was the best individual contributor on his team. The same selection process happens in most fields—private or public sector. The best accountant is promoted to lead the other accountants, the best programmer is promoted to lead the other programmers, the best salesperson is promoted to lead the other salespeople, etc.
So, if you’re like Matt, congratulations. You’ve been promoted to supervisor. Now what? Like most first-time bosses, you’ve probably had little or no formal leadership training. Perhaps you’ve had minimal guidance from your employer as to how you should lead or the type of work environment you should create. In nearly two decades as an executive and ten years as an executive coach, I’ve noticed that a few new bosses thrive in their new role, some survive, and many struggle to keep their heads above water. What I’ve discovered along the way are common threads—and some particularly effective skills—that help new bosses thrive in new leadership roles.
A big challenge for many first-time bosses is recognizing that the knowledge, skills, and abilities that earned their promotion are only part of what they need to succeed in their new role. Yes, individual contributor excellence is important, but continuing being the best analyst, accountant, programmer, or salesperson does not make someone a good leader.
The answer to this challenge is fairly simple: Successful leadership requires new ways of thinking about yourself and new ways of acting. This Guide will describe a dozen key leadership skills, teach you how to use those skills, offer ways to hold yourself accountable for using those skills, and suggest additional resources for those who want to learn more.
Shift To Developing Great Individual Contributors
Successful first-time bosses quickly learn that to build a strong team, they should focus on two objectives. They must develop their team members to be more effective—rather than making themselves more effective—and create a healthy work environment. The question is how?
The first step is to shift your mindset from being a great individual contributor to being a developer of great individual contributors. Your knowledge, expertise, and drive earned you pay raises, bonuses, recognition, a promotion, and maybe even a bigger office or a better parking space. But ask yourself, which will be more effective in the future—increasing your personal productivity by ten percent or helping each of your team members increase their productivity by ten percent? Liz Wiseman has a great name for leaders like this in her book, Multipliers, How the Best Leaders Make Everyone Smarter. She describes a “Multiplier” as “the leader who sees, provokes, asks, and unleashes the capabilities of others.”
I’m continually amazed by how few new supervisors receive any leadership or management training, formal mentoring, or coaching to help them become the kind of “multiplier” who develops stronger team members and better teams. New supervisors, however, shouldn’t despair—helping your team members reach their potential and create a great work environment begins with and depends on conversation. The more effective your conversations, the more effectively you can develop people. I’m convinced that anyone can do it if they learn and employ the skills described in the following pages.
As authors Chalmers Brothers and Vinay Kumar make clear in Language and the Pursuit of Leadership Excellence, nearly everything that occurs in the workplace is the result of a conversation. Leaders are paid to have conversations. Lots of them. Conversations are how we:
● Create relationships
● Build trust
● Share information
● Assign work
● Teach and are taught
● Set and enforce accountability standards
● Shape culture
● Listen to, and learn from and about, our team members
Conversations take on additional importance in the hybrid, work-from-home era. Conversations keep team members feeling connected when so few opportunities for informal, spontaneous conversations exist. There are fewer quick chats in the hallway, by the coffee pot, or before and after in-person meetings. No matter where your team members work—from home or in the office, full or part-time—it is important to make the most of every conversation, whether in-person, on the phone, or via Zoom or Teams.
In their book, Nine Lies About Work, authors Marcus Buckingham and Ashley Goodall posit that a manager must have at least one brief conversation per week with each direct report, during which two key questions should be asked:
● What are your priorities?
● How can I help?
They also state that if a manager does not have time to hold these conversations, they have too many direct reports. Such conversations are the bare minimum necessary to keep employees engaged, to build trust, and to create opportunities for their development. They also show your commitment to their growth and your interest in their challenges.
So how do we make our conversations and our efforts to make our team members as productive as possible? The Dozen Key Skills are here to help.
The Dozen Key Skills
I tell every coaching client that I don’t have a pre-conceived plan to make them an amazing leader, because there is no one-size-fits-all path to great leadership. Every leader possesses their own unique strengths, challenges, and personality traits. Only individuals can determine what will work best for themselves and their team. The most successful new leaders I’ve worked with, however, use most or all of the following skills to foster conversations that are vital for building strong teams, and to help their team members reach their full potential.
I call these The Dozen Key Skills:
● Listen to understand.
● Ask questions to encourage thoughtful discussion.
● Provide feedback that encourages thoughtful action.
● Delegate challenging work.
● Establish clear accountability standards.
● Overcome fear of tough conversations.
● Encourage innovation.
● Inspire commitment.
● Articulate your authentic leadership style.
● Foster a healthy work environment.
● Lead former peers.
● Imagine the future.
These skills are not rocket science, nor are they out of reach. Everyone can learn them. Everyone can implement them well. Each of the dozen skills is based on common sense and human nature. Some may come naturally. Some won’t. Each skill is useful by itself and even more useful when applied in conjunction with the other skills.
Each of the following chapters examines a skill and describes:
● Why the skill is important;
● How to implement the skill;
● A related story or example;
● How to hold yourself accountable for using the skill; and
● Where to find additional information.
All of these skills can be mastered with a bit of effort and self-awareness. And of course, the necessary investment of time—time to commit to your own growth as a leader.
Get Off Autopilot
To fully develop any, or all, of the above dozen key skills, one global skill is common to all good leaders: self-observation.
Most people go about their workday on what I call “autopilot.” They act out of familiarity, out of comfort, out of routine. Being on autopilot can be highly efficient. When we don’t think about how we want to “be” or relate to others, we can devote more mental energy to what we want to do. The problem is that being on autopilot inhibits the growth of leaders. Doing what we “usually do” might not get the best results from a conversation, a meeting, or a situation. It keeps us from thinking creatively. Conversely, the more aware we are of our own behavior, the better chance we can adjust our speech and/or actions to get improved results from the people we work with or the situations we encounter.
How does “getting off autopilot” work? One popular analogy is to virtually “go to the balcony,” and pretend you are looking down and observing yourself in action. Or imagine you are videoing yourself. The idea in both examples is to devote part of your brain to observing how you are: Are you calm or stressed? Listening well or talking too much? Speaking appropriately? The more we observe ourselves, the more often we can adjust our behavior, if necessary, and the more often we can get the results we want.
Another self-observation technique that works well is to treat yourself as a science experiment, one in which you are both the subject of the experiment and the scientist. What data could you record that might help you lead more effectively? A few questions to ask yourself include:
· How many times per week do I give feedback?
· What percentage of the time do I talk when leading a meeting?
· How often do I meet with team members one-on-one?
· How often do I connect team members’ work to key mission goals?
· Am I micromanaging? Or giving too little guidance?
· What work am I performing that could or should be done by a team member instead?
· What causes me stress in the workplace?
· What gives me joy? And how do I increase that?
· Under what conditions am I most productive?
In addition to expanding upon the Dozen Key Skills, each of the following chapters suggests potential self-observation exercises. Once mastered, you will be able to assess your behavior and hold yourself accountable for almost anything. Use your imagination and decide which behaviors will be most useful to observe in your leadership development journey and search for the easiest way to collect relevant information. Options range from making check marks on a Post-It note to extensive journaling. There’s no right or wrong. If it is something you will implement and find helpful, go for it.
Skill 1: Listen To Understand
Speaking well is probably one of the reasons you were promoted. But being a great speaker does not, by itself, make someone a good leader. The best leaders are also great listeners. Listening is how leaders learn about their team members, their work, and the challenges they face. Listening well is essential for productive conversations. It’s fundamental to building good relationships and it’s hard to lead effectively without good relationships. There’s a reason we have two ears and one mouth. We don’t learn when we speak.
Any Google search would reveal many definitions of effective listening and numerous techniques for improving these skills. All can be boiled down to the simplest level: do we listen to understand or do we listen to reply.
The vast majority of the time, the vast majority of us formulate what we want to say while our conversation partner speaks. This is listening to respond. The nature of business tempts us to convey information quickly, advocate for our priorities, and persuade others how right we are or how wrong they are. Typically, we impatiently wait for others to stop talking before agreeing, disagreeing, or explaining. While this may feel efficient, we end up missing so much. By paying attention to our own thoughts instead of hearing our conversation partner’s words, we often fail to understand fully what the other person is saying, and more importantly, why they are saying it. Jason Headley’s video, “It’s Not About the Nail,” (available on YouTube) is a great example of listening to respond when listening to understand is what his conversation partner needs to feel heard.
There’s a better way. Listening to understand requires that we silence the soundtrack in our mind while the other person talks and recognize that we don’t need to spring-load a response to launch as soon as the other person pauses for breath or stops talking. There’s nothing wrong with waiting for a few seconds before we speak—such a silence gives us time to process and think of something to say—and what’s the big deal if there are a few seconds of quiet? When we talk less and listen more, we learn more information from the other person and more about the emotion and the reasoning behind what they say.
Good listening builds relationships. Being fully present and giving another person our full attention is a great gift and meets a deep, universal human need to be heard and feel valued. It strengthens our work relationships and builds trust. The stronger our relationships and the more team members trust us, the more they will let us lead them.
A colleague of mine in the 1990s is the most striking example of great listening to understand that I’ve witnessed. Phoebe was a deep listener—giving her full attention, asking inviting questions, maintaining eye contact and a relaxed posture, and letting her conversational partner finish their thoughts—who made people feel truly heard and valued. I jokingly told colleagues she must be an alien, who had an infra-red beam that shone from her forehead and bathed people in a warm glow! At one point, she and I competed for a big promotion. I had more direct job experience and subject matter expertise, but my boss chose Phoebe for the promotion. In addition to being smart, hard-working, and persuasive, her deep listening to understand created powerful executive presence, built strong relationships, and exerted a gravitational pull on colleagues. “Listening to understand” was likely a key element in her rise to be CEO of a corporation with annual revenue of $38 billion. Guess my boss made a pretty good selection.
Were Phoebe’s deep listening skill and executive presence natural gifts or did she learn? I never asked her, and I suspect her talents were a combination of nature and training. In his book Supercommunicators, Charles Duhig describes how the Central Intelligence Agency trains its’ operations officers to listen deeply and ask open-ended questions to create the connection and trust necessary to recruit foreign citizens to spy on their own country on behalf of the United States. His book is well worth reading and as you might have guessed, Phoebe had been a CIA operations officer.
Early in my career as a manager, I spoke too much and didn’t listen enough. For a typical staff meeting, I would arrive with a long list of information I wanted to transmit. By the time I finished talking, we were usually running out of time and few team members had a chance to speak. I was doing all the work and probably boring my team members. And, most importantly, I did not learn information my team members could have contributed. After reflection, I did what lots of effective leaders do: I copied a technique of a leader I respected. The Admiral for whom I worked would wait to talk until after everyone else had a chance to speak, allowing him to consider others’ information and opinions before making concluding remarks or decisions. I implemented this technique, which I called the “Reverse Order Meeting.” I still arrived with a long list of items that I wanted to ensure were covered, but instead of doing most of the talking, I let everyone else update the team about their work. All I had to do was comment or add missing information as needed. Invariably, by the time we’d gone around the room, 90 percent of the topics on my list had been addressed. I talked less, learned more, and all I had to do was comment on a few items raised by team members or say, “Thank you.” Most importantly, my team members felt empowered and valuable.
There are all sorts of ways to practice and/or hold yourself accountable for listening to understand. The key is to collect information as easily as possible and in whatever way will be most useful for you. A few ideas that have worked for my coaching clients include:
· Reflect briefly after each conversation and note if you were listening to respond or listening to understand. You can collect data about your listening style and skills on a simple Post-it note or record it in a larger document after a meeting. Try to discern patterns in what helps or hinders your listening or even note with whom you succeed or struggle when listening to understand. A few days’ worth of data may be very revealing.
· Observe and note how people respond when you listen to understand.
· Ask a team member or colleague to track how much you speak compared to others in meetings.
Listening to understand is a challenge. Don’t be discouraged if you find yourself listening to understand and then sliding back to listening to respond. Rather, be encouraged that your self-observation skills are working and you are noticing how you are listening. This is a key step toward great listening as a leader.
To learn more about effective listening, I recommend the book Language and the Pursuit of Happiness: A New Foundation for Designing Your Life, Your Relationships & Your Results by Chalmers Brothers. At first glance, it may not sound like a book about leadership or business, but dive in. It is a fantastic resource for improving your conversations, and that will get results.
Skill 2 - Ask Questions That Encourage Thoughtful Discussion
Asking questions becomes increasingly more important the higher someone climbs the organizational ladder. Questions help us gather information to make better decisions, uncover alternative courses of action, encourage innovation, and challenge team members to think for themselves. Given the importance of asking questions, it is surprising that few new leaders—and even experienced ones—think intentionally about how they ask questions or strive to do it well.
Humans are stubborn. We are more likely to respond positively and productively when we get to decide what we want to do instead of being told what to do or how to do it. When my granddaughter was three and I asked if she needed to go the bathroom, she invariably said, “No,” even when the signs were clear that she needed a bathroom visit. If, however, I asked her which bathroom she wanted to use, she would choose and visit the bathroom with minimal fuss. Adult team members aren’t much different than three-year-olds when it comes to their desire to decide for themselves.
The most effective questions are ones that invite thoughtful responses. Many of us unwittingly ask “close-ended” questions that can be answered with “yes,” “no,” or other one-word answers. Open-ended questions elicit longer responses and encourage more thought from the person we’re questioning. If we ask a team member, “Are you making good progress on your project?”, they easily could answer, “yes” or “no”—and we won’t learn much. Asking questions such as, “What progress are you making on your project?”, “What challenges are you facing?”, or “Would you tell me about your project?”, invite more thoughtful and certainly more informative responses.
The most thoughtful questions tend to be brief and non-judgmental, and they require significant thought to answer. They usually begin with “how” or “what.” Be on alert when asking a question starting with “why,” which can be perceived as accusatory or judgmental, particularly in an email or text in which the reader doesn’t have access to the tone of our voice or non-verbal cues. Examples of simple, effective questions include:
● What options are you considering?
● How do you plan to proceed?
● What’s on your mind?
● What led to that conclusion? (Much more inviting and less judgmental than “Why did you do that?”)
You are most likely on the wrong track if your questioning resembles a Congressional hearing, in which a senator takes five minutes to make a statement and concludes with a question such as, “Why did you do that?” or “Do you still kick your dog?”
It is very easy to fall into the “expertise trap,” which occurs when a team member asks a question that tempts you to show how much you know. Although you truly may be the expert, it is often more important to develop other experts or draw out your team members’ expertise than demonstrate your own brilliance. Rather than answering the question, or giving guidance, consider asking questions to challenge your team members to think of solutions themselves. When team members ask you to make a decision, consider suggesting that they take the reins or, at a minimum, that they make a recommendation and discuss the pros and cons with you.
Steve—a senior attorney and nationally recognized expert at a federal regulatory agency—tired of seemingly endless debates with fellow attorneys. He decided to experiment. Instead of trying to persuade other attorneys to adopt his point of view, he began asking open-ended questions. He found that the more open-ended questions he asked, the more other lawyers spoke. And the more they spoke, the more likely they were to talk themselves into adopting his point of view. The senior attorney said, “I love it. I talk less and I win more debates.”
To hold yourself accountable for asking effective questions, consider:
· Noting the number of open-ended and closed-ended questions you ask in a week.
· Making a list of every question you ask for several days.
· Asking a trusted colleague to track the number and type of questions you ask.
· Practicing by asking your kids open-ended questions. Instead of: “Did you have a good day at school?” ask “What was the best thing that happened today at school?” or “What’s the most interesting thing you learned today?”
You may be surprised how quickly such simple observations build new, productive habits for you while also bringing out the best from team members. You also may want to pay attention to how your team members respond when you ask open-ended questions.
The book Change Your Questions, Change Your Life, by Marilee Adams, is a great resource to learn more about how to ask effective, non-judgmental questions. And The Coaching Habit, by Michael Bungay Stanier, is a superb guide to asking questions that lead team members to think for themselves. Both books are short and easy to read—and full of practical suggestions.
I love to help leaders grow
Technical skills only get you so far. "Soft" Skills Determine Who Rises.
I'm an International Coaching Federation Master Certified Coach and former CFO who'll be your partner in refining your "soft" skills so you can overcome the day-to-day frustrations of managing so you can develop your people, build high performing teams and succeed as an executive by:
- Enhancing your self-awareness
- Increasing your emotional intelligence
- Strengthening your listening and communication skills
- Honing your unique leadership style
- Refining and communicating your strategic vision Inspiring employees
- Delegating effectively
- Delivering effective feedback
- Developing employees
- Building trust among superiors, peers and employees
- Making conflict less stressful and more constructive
- Creating a healthy office environment and engaged workforce
- Enhancing your executive presence
- Asking more effective questions