The Two Leaps of Leadership

Becoming a leader is awesome. You enjoy a direct hand in developing people and helping them achieve new heights. Few things are more fulfilling in professional life.

Naturally though, the challenges are numerous. While everyone follows their own leadership journey, nearly every leader faces common pitfalls along the way.

Two inflection points (or leaps) exist along that journey. The first leap involves moving from an individual contributor to a leadership role. Most leaders start the journey here.

The second leap involves becoming a leader of leaders. This is equally as challenging, and not everyone reaches this point. Less literature exists covering this domain, despite the stakes being even higher.

Let’s look at common challenges during both leaps.

Leap #1: First Becoming a Leader

The first step into leadership is both exciting and daunting. Likely, you demonstrated excellence at a particular task or discipline, leading to your promotion. Congratulations on your higher pay… and higher expectations.

Your new mission: guiding a team and developing new versions of you. You are measured not only by the efficiency of your own work, but the effectiveness of the entire team.

There are several new challenges and pitfalls to prepare for. This list is by no means exhaustive:

Pitfall #1: Doing the work for your team
Nearly every leader (new and old) falls into this trap, repeatedly. Consider – you were excellent at a particular task. You observe a member of your team struggling with that task. Perhaps you can do it better or faster, so you swoop in and complete the task for them. You may even think you did the right thing, by “showing” them the correct approach. Job well done, right?

Wrong. Showing them once may be fine. But leaders often feel pressured to jump in frequently. Teachers do not complete homework or tests for students. Similarly, your responsibility as a leader is to guide, answer questions, and pick people up when they stumble – not to do the work for your team members.

Why should this be avoided? The reasons might be obvious:

• Your team members will not learn and grow
• Your team may resent you, become lazy, or dependent
• You will burn yourself out

…and yet, it still takes enormous willpower to not jump in. Stay vigilant, and check yourself if you start to slip.

There are exceptions where jumping in may be ok:

• The impact of not jumping in will be catastrophic (i.e., imminent collapse of a project, system, company, etc.). Be wary though – is something truly so urgent that you must take direct action instead of providing support and guidance? Or did you place false urgency just to be a hero?
• Your team faces an overwhelming amount of work. In that case, you are not completing work for a team member, but instead pitching in to share a huge workload. If this is a long-term condition, you have a team capacity problem to address.

One of the greatest rewards of being a leader is helping people grow. Don’t deprive them of that. Don’t be the hero. Create a team of heroes.

Pitfall #2: Not understanding that relationships change with (former) peers
Congratulations again on your promotion to leader. Everyone who worked with you now works for you. You had strong personal friendships with your peers before. Those relationships remain unchanged, right?

Wrong, sadly. This is a painful but necessary truth. People who were friends before are now employees. That is now the primary relationship. You cannot play favorites. You cannot create the reality or perception that one person is treated differently because of friendship. This requires constant self-reflection and vigilance. This covers not just actions you take, but also how you approach conversations. People are observant. The first sign of favoritism will lead to disaster.

You can remain (or make) friends with people that report to you. Some leaders subscribe to a complete social or personal separation from those that report to them. That may work for them. However, the line does not need to be that stark. It is human nature to form personal relationships.

Lunches, after-work drinks, and similar appropriate social events are fine. The key – it must be equitable, open and encouraged for all. Apply common sense to appropriateness. If you go on vacation with a team member, what message are you sending to the rest of the team? Likely not a good one. If there is ever doubt, error on the side of caution.

The adjustment to leader is not just difficult for you. Friends must now recognize you as their leader first, friend second. This can be especially challenging during direct conversations. Providing critical feedback will be difficult and possibly emotional. Your relationship may even be leveraged against you: “I thought we were friends!”

Honesty and openness are pivotal. Talk about this new reality upfront. Acknowledge that the relationship will change. Acknowledge that both parties must adjust and behave professionally, both in action and conversation. Advise that there will be direct conversations, where needed. This will (hopefully) prevent shock when it happens.

This is not an easy dance. You must preserve authority and professionalism as a leader. You must avoid favoritism. Certainly, you prefer to maintain personal relationships along the way. Be vigilant and equitable. As with most things, acknowledging this openly will smooth out the transition.

Pitfall #3: Ignoring resentment from others passed over for promotion
Consider a common scenario – a leadership position opens on the team. You and another person on the team apply for it. You win the role. The other person who applied now reports to you, with unknown levels of discouragement or resentment from being passed over. What do you do?

Certainly do not ignore it, expecting it to disappear. You risk letting it fester, damaging your long-term relationship with that person. Do not gloat or be insufferable either. No one wants to hear any flavor of this: “Be an adult and accept it. Move on.”

Instead, tackle it head on with sincerity and sensitivity. “I know you were up for this position too. I recognize it’s tough not getting it. Whatever you want to discuss, I am here to listen. Hopefully we can both work hard to minimize any unease, then work together to get you into this role in the future.”

Honesty and empathy provide the best chance to preempt any resentment. It may not always be successful. The person may even decide to move on. Such is life. As the leader though, make the first move.

Pitfall #4: Failing to set clear expectations
Good leaders embrace clear and direct communication. People crave clarity around expectations and direction, for both the team as a whole and them as individuals.

A new leader always brings some uncertainty for a team. Will expectations change? Will I be able to achieve them? If left unaddressed, concern will grow and trust will erode. Chronically unclear expectations create a rudderless, unmotivated team.

Perhaps you need time to formulate a plan and the expectations around it. That’s perfectly okay. Be upfront with your team. Set and share a reasonable timeline for this exercise: “I need XX days to gather data, and another XX days to put a plan together.” Strive to meet that timeline. Involve the team in the development where appropriate – a great way to generate excitement and buy-in.

Share the finished plan in a team meeting. Ensure team goals are clear, measurable, and documented. Follow this by setting individual expectations in one-on-one meetings. People want to know not just the overarching direction, but the part they will play (and ultimately how they will be measured). If this is not clear to you, it will not be clear to them.

Above all, be direct. Do not avoid difficult conversations. Directness does not mean rude or authoritarian. It means getting to the point, quickly and concisely. Do not cushion or obfuscate tough messages – people see through this. Say things as they are. This builds respect and trust.

Never surprise your team either, if in your control. Setting an expectation and then pivoting during performance reviews will destroy your credibility. Changes to plans, goals, and expectations will happen. Inform your team quickly and thoroughly. Help them understand the what and why. Change is not always embraced, but this approach provides the best chance to limit frustration.

Pitfall #5: Expecting your team to work exactly the same as you
You were promoted for a reason. You are blessed with considerable experience and expertise. Naturally, you must always know the correct approach, right?

Not so fast. The goal is not uniformity. The goal is success and efficiency. A leader should absolutely drive clear expectations and set guardrails. You will often provide guidance on good practice, perhaps standardizing processes to ensure repeatability.

However – within those guardrails, always encourage flexibility to achieve team goals. No person wants to be micromanaged or stifled. No two people work alike. Diversity of mindset and tactics spurs growth and avoids groupthink. Think what awesome innovation a team member may discover if unleashed!

There is a balance. You must discern what is ineffective versus merely different. Provide corrective guidance for the former (clear metrics help). Encourage the latter. It can be scary to “let go” and empower a team. Ultimately, both you and the team will reap the rewards.

Pitfall #6: Letting others pile on your team
Most organizations are busy. Your team likely supports multiple processes or projects. Even at mature organizations with established process around work flow (like Agile), chaos often reigns.

Let’s look at a common scenario. You and your team map out work over an upcoming time period. This plan lasts exactly 2 hours – nothing ever goes according to plan. Another team or leader swoops in, needing support. Frustratingly, they bypass you and go directly to your team. They may exert pressure: “This is vital XYZ project, drop what you are doing and help me now!”

Do not allow this. New or unexpected work must always flow through you, not directly to your team. You must ensure the priority and allocation of that work versus existing work.

Set this expectation with other leaders and teams. Encourage your team to politely escalate any requests that bypass you. Never force your team to judge whether to continue with planned work, or jump to new work. That’s your job.

This can be tricky. You and your team want to be helpful, not roadblocks. However, without structure, everything slows down. The goal is to do the right work. The most valuable work. Not appease the loudest demand. That is a discussion and decision between leaders. If a change of plan is agreed upon – great! You can then set the new expectation with your team.

Always serve as that buffer. Protect your team from unnecessary stress. Let them focus effectively on the work you put in front of them.

Pitfall #7: Letting <blank> roll downhill
Every person, including leaders, have tough days. Pressure and stress may be high. Perhaps you had a rough interaction with another leader or team member. Perhaps you received critical feedback or bad news from your boss. Or maybe you had to address some organizational conflict. Leaders get put in difficult situations.

We are all human. It can be hard to compartmentalize. But a leader must not propagate stress or frustration downhill to their team.

Your team is perceptive. They will recognize if something is wrong. Do not lie to them, or put on fake cheeriness. But do not vent to your team. Do not throw other people under the bus. Do not wallow in negativity. Your team will take their cues from you and behave accordingly.

Instead, find learning lessons out of tough situations and share that with your team. That may not be easy, especially if your own emotion is raw. Take the time to digest the situation and compose yourself first. Find the positive hiding within the negative.

This is a mindset, and by no means simple. The benefits though will be huge for you and your team’s psyche.

Leap #2: Becoming a Leader of Leaders

With experience, your proficiency grows as a leader. Eventually, you prove your excellence guiding and developing your team. Another promotion comes your way – this time to manage multiple teams. Instead of managing individual contributors, you will now lead other leaders.

Congratulations on achieving this second step! All previous challenges still exist, with more sprinkled on for flavor:

Pitfall #1: Failing to give your leaders enough autonomy
Recall the theme from earlier. No two people work alike. Similarly, other leaders will lead differently than you.

Your new responsibility is to provide org-wide direction, expectations, and guardrails. Grant your leaders the authority and flexibility within their teams to achieve those goals. Measure them against results, not necessarily methods (assuming their methods are professional and ethical). While you may still get involved in the how, strive to let your leaders drive the ship.

Remember to let leaders make mistakes. Trial and error leads to growth. Do not stifle that learning experience. Provide guidance and a safety-net as needed – preferably by serving as an escalation or sounding board. Like individual contributors, no leader wants to be micromanaged. Do not dictate every action or step along the way.

Step in directly only if something catastrophic will happen. Do not set up your leader for embarrassing failure. You are still accountable for success. Try to accomplish this without damaging the credibility of the leader. Pull them in privately and set corrective action. Let the leader then drive that action, as if it’s coming from them.

Knowing when to step in can be difficult. Try not to sweat the small stuff. Focus on mistakes that have a multiplicative effect – big purchases, sensitive personnel issues, or broad communications. Use these situations as teaching experiences.

Pitfall #2: Skip-level managing
Consider – you need a small project done, or some information gathered. You know just the person in your org-tree who can help. Why bother their leader when you can go directly to that team member? Naturally, they jump to help. You are their leader’s boss – they want to make a good impression. Harmless, right?

In reality, this disrespects both the leader and their team member. What work will your request interrupt? The team member will likely not feel comfortable objecting to the interruption. If the leader is unaware of your request, they cannot prioritize and manage the workload of their team.

Always consult with the leader first. Ideally, pass any request to the leader, and let them execute with their team. Sure – their team is technically your team. Do not abuse this. Respect your leader and allow them to do their job.

Skip-leveling is not limited to assigning work. Avoid providing feedback directly to a team member while bypassing their leader. You can make an exception in acute situations – i.e., obviously inappropriate behavior that needs to be addressed immediately. Otherwise, pass the feedback to the leader and allow them to performance manage accordingly.

Ultimately, skip-level managing has two detrimental effects:

• The leader you are ‘skipping’ over will lose credibility with their team. The team will question why their leader is being bypassed. They may assume you have no confidence in their leader.
• The leader will resent you, or lose confidence. No doubt, they will question why you do not respect their ability to manage the performance and workload of their team.

Ask yourself – what compelled you to skip-level manage?

• Because you want something right now? Barring an emergency, this is never a good reason to undermine your leader.
• Because, in actuality, you lack confidence in the leader? Address that performance issue directly with the leader. Stop creating an uncomfortable situation for them and their team.

Put yourself in that leader’s shoes. Treat them as you wish to be treated by your leader.

Pitfall #3: Failing to adjust being further from the work.
Becoming a leader of leaders can feel eerie at first. You are much further from the front lines. You cannot shake the feeling of being disconnected. Are things going well? Are there problems you are unaware of?

You are not alone with these thoughts. It is tough to strike the right balance between granting autonomy to your leaders and staying connected.

Remember to focus on outcomes and not methods. Set the goals. Ensure they are measurable. Where possible, let your leaders drive the how. In your leader meetings and one-on-ones, review the progress towards those goals.

You will still feel disconnected. How can you stay informed on the health of your entire org-tree? Metrics and leader discussions give great indicators. Other tools are also at your disposal:

• Anonymous surveys: Keep these simple and short. What is going well? What needs to be changed? Hopefully people are forthcoming and give you broad insight.
• Skip-level feedback sessions: More time intensive than a survey, but generally yield more specific information. People may be quiet or uncomfortable at first. Try to gently ask questions to stir conversation. Then stop talking, listen, and take notes.

Note that skip-level feedback (where you listen) is different than skip-level managing (where you give orders). Regardless, inform your leaders before performing any survey or skip-level session. Do not surprise them. Share themes with them. Your leaders likely crave this information as much as you, and want to take action.

Separately, maintain an open-door policy for anyone to talk to you. Listen to concerns. Still be mindful of skip-level managing. Gently ask if they brought the concern to their leader first. If not – why? This could be indicative of a trust problem in your org-tree. If yes, why did they also escalate to you? Was no action taken? Is there disagreement on the importance of the concern?

Assure the team member you seek to understand, and not to deflect. Where possible though, encourage the team member to work with their leader to resolve the situation first. Restoring that bridge is paramount. If they cannot, then get involved and take action.

Pitfall #4: Failing to set a compelling vision for your org-tree
Remember, everyone wants clear expectations. That is “table stakes” for a good leader to provide. Beyond that, people crave a compelling vision to rally behind. They look to the higher levels of leadership. Nothing galvanizes a team more than an exciting and ambitious direction.

What happens if vision is lacking?

• An unclear vision will cause confusion and eventually indifference
• Too small-scale a vision will frustrate your highest performers
• Too broad a vision will be difficult to manage and make progress

One caution – people love to chase the “latest thing”, such as the newest technology or business trend. Perhaps this is exactly the right direction for your org. Be thoughtful though – vision and direction must always tie to business goals.

Adopting the trendy ‘thing’ may please people – temporarily. However, without a meaningful plan or business relevance, you are wasting time and money. Executive leadership may not be pleased with the misuse of corporate resources. Vision must always be practical and relevant (though it can still be ambitious).

Align with your leaders first before communicating a vision to the entire team. Give them time to digest, ask questions, and anticipate their team’s reaction. Once onboard, your leaders will serve as lieutenants to manage adoption across your org-tree.

Closing Thoughts

Do not be deterred by these pitfalls. Being a leader is still awesome. Take comfort – every leader faces most or all of these challenges. We all make mistakes (me especially). There is no magic bullet. Learn by doing. Make those mistakes. Be self-reflective and grow.

Also, you are not alone. Build a support group of other leaders. Be transparent with each other on struggles. Help each other. The bonds you forge will be a powerful resource.

You got this. Best wishes in your leadership journey!

© 2024 Aaron Balchunas
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