In my recent professional career I’ve worked at the elbow of supervisory and management-level leaders in a coaching and learning facilitator capacity. Over the years I’ve witnessed management blunders, triaged ailing team dynamics, coached leaders to be the antidote to toxic situations, and supported those who seemed to be cracking under the weight of their role. Supervisors and managers are pivotal to almost every aspect of an organization’s success, for it is they who either oxygenate or suffocate buy-in, commitment, collaboration, and excitement one individual at a time. These roles are also pivotal to team relationships and employee development, engagement, and accountability. Indeed, mid-level leadership is about three things: emotional intelligence, grit, and nurturing relationships. It is not for the insecure, immature, or impatient.

This article is not intended to tell you how to be a successful manager. There are plenty of books and articles that claim to do that. This article is intended to be a bit of a cautionary tale cum reality check. It is intended to pass on—in the form of insightful questions to ask of yourself and your organization—advice that I believe will allow you to be honest with yourself about your readiness to accept a mid-level leadership role. Each question has its roots in the weeds I’ve witnessed managers water or not be prepared to eradicate. They stem from my observations about the tipping points where managers and supervisors either fail or succeed.

Questions to ask as part of the interview process:

  1. What is the organization’s accountability model? If the answer you receive involves nothing more than increasingly punitive corrective actions, be prepared to be the bad guy. If the answer doesn’t also mention assumption of positive intent, coaching, mentoring, or systemic and process analysis, learn to love rules and be prepared to enforce them.
  2. What is the level of accountability on the existing/inherited team? Whatever the organization’s accountability model, you should know going in whether or not the leader before you held anyone accountable. If you inherit a team whose prior leader chose the friend path and let people get away with questionable behavior and performance, prepare yourself for some seriously heavy lifting. It’s hard to be seen as the bad guy; unfortunately, when you begin to hold people accountable that is often the short-term result. But chin up! In the long run, those employees who are engaged and committed will appreciate your expectations and efforts. It will prove you’re trustworthy and reliable, which in turn, will earn you the trust of the type of employees you want on your team. To learn more about holding others accountable in a positive, principled way, check out Roger Conners’ How Did That Happen?
  3. If you discover there’s little to no accountability, ask yourself, “Am I ready to hold people accountable, for better and worse?” If the answer is yes, then ask “What support will I have from you when I start to hold people accountable?” If you can’t keep the long term benefits mentioned above in your sights and don’t have the support of your leaders, the short-term unpleasantness and stress will break you. Seriously.
  4. What are the key results you will be responsible for? In order to hold yourself and others accountable, you need to set clear expectations. In order to set clear expectations, you need to know what you and your team will be expected to deliver. This goes beyond the details of a job description. It requires some big picture vision to understand how your department, your role, and your team fit within the organization’s business strategy. Only then can get down to strategic thinking and implementation within your realm of influence. If you doubt the importance of setting and communicating clear expectations, check out Patrick Lencioni’s The Five Dysfunctions of a Team. If you’d like to learn how to form, communicate, and examine your expectations, check out Roger Conners’ How Did That Happen?
  5.  What does the existing team need to celebrate or grieve? Unless you’re walking into a brand new team where no one has worked together before, you’re walking into a team with history. They have a culture with norms, expectations, and tacit assumptions. Maybe they had a leader they loved…or hated. Maybe that leader did wonderful things…or terrible. Either way, people need a chance to transition, to celebrate, and to make peace with what was before they can buy-in to what will be. To learn more about helping yourself and others navigate change, check out William Bridges’ Managing Transitions.

Questions to ask yourself before you accept the job offer:

6. Am I ready to lose friends? Because you will. This question is specifically for those of you going From Bud to Boss within your current team. Transitioning to a leadership role means current friendship dynamics will have to change if you want to be successful. Though certain friendships you had as an individual contributor may lessen, new friendships and support systems will develop and grow.

7. What are my top 5 leadership values? Can I articulate them? How will I
communicate them?
Your leadership values are those that guide your thinking,
your decisions, your behaviors, and your vision for the team. If you can’t name them right now, you need to do this work before you accept the leadership role. You will be faced with difficult decisions. Policies and procedures might guide you; the organization’s values might also guide you. But the clearest guide are your leadership values. Check out my prior blog post for links to values discovery exercises.

8. Am I a fixer? Many people accept a supervisor or management position because it reflects an opportunity to share hard earned experience, wisdom, knowledge, and lessons learned. Indeed, the promotion may have come your way because you frequently had all the answers or could fix most problems. And therein lies the management rub: one of the things that earned you the leadership role is one of the things that could undermine you and your team. If—when your team comes to you with problems—you always have the answer, always share an opinion, and always have guidance and direction to give, you unintentionally create directionless, disempowered, and disengaged people. Not to mention a whole lot of stress for you. I once had a manager candidly say that she couldn’t attend an all-day learning session because her team couldn’t function without her—work would stop. If that’s true, rather than a simple egotistical statement, this manager is going about management all wrong. The idea is to create an engaged and empowered environment where a manager’s clear trust and expectations support the contributor’s clear ownership and ability. The more you fix, the more answers you give, the less engaged and empowered your team will be. Say bye-bye to vacation!

9. How do I feel about feedback? Because you’re going to get it. And get it some more. And then some more. If you’re lucky, it will be delivered almost real-time with respect and support. If you’re not lucky, it will fester and sideswipe you in an annual review. Oh yeah, did I mention you’re going to have to give feedback too?

How will you handle feedback that compliments you? Learn to accept praise, and to give it. This isn’t easy for everyone, but everyone needs it.

How will you handle feedback that challenges the way you see yourself? Note to you, you’re not perfect. And if you say to me, “Jenny, I know I’m not perfect,” I’ll say in return, “Good, but you’re not perfect in the ways you think you’re not perfect.” There’s a whole unknown world to you of how you’re imperfect and your contributors will discover, map, and name the ways you’re not perfect. If you’re lucky (and okay with being vulnerable), they’ll share this with you sooner rather than later. If you’re not lucky, guess what? Fester fester fester…sideswiped again.

Keep this sideswiping in mind as you consider that you will have to deliver the same kind of feedback to others in order for them to grow, develop, and excel. Please, don’t be a sideswiper boss (!), the kind who avoids regular check ins and feedback opportunities and instead delivers delayed, useless, and non-actionable feedback disguised as an annual review. Need help on giving feedback? Check out an InsideOut Coaching workshop near you and dive into Kim Scott’s book Radical Candor or one of her many Youtube videos by the same name. Here’s my favorite.

Lastly, how will you handle feedback that contradicts other feedback? Your leadership values should help guide your consideration of this question. Remember, your values guide your thinking, your decisions, and your behaviors. When you can’t please everyone, you have to go back to your values. Are you behaving in alignment with them? If so, communicate that to your team. If not, reexamine your actions, be open to being vulnerable, then learn, grow, and realign. If I could pass on one pearl of wisdom it is to remember that feedback is more often reflective of the deliverer rather than reflective of you. Feedback isn’t always a personal attack; feedback doesn’t always have to result in a change on your part. Go in with humility and with curiosity to understand.

  1. Am I ready to deal with adolescent behaviors? The biggest jaw dropper observation in my professional career has been the gaping dearth of emotional intelligence and maturity exhibited in humans masquerading as adults: taking things personally, exaggerating, gossiping, this is mine/that’s yours nonsense, downright rude and thoughtless behavior. I’ve been dumbfounded, demoralized, and disgusted on several occasions. I don’t get it. I don’t even have any guidance beyond this: If you walk into a team like this, don’t contribute to it by tolerating it.

Mid-level leaders are the lifeblood of an organization. I wish more organizations recognized this and devoted more time, more money, and more thought to supporting and developing managers and supervisors. Unfortunately, they’re often chewed up and spit out. I don’t want any more great people to end up a half-eaten entrée. Hopefully, giving consideration to the questions above will help you decide if you should even be on the menu.


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