5 Hard Truths about Making the Leap to Leadership
June 18, 2026 | By David M. Wagner
I remember the first time a peer was promoted before I was.
His first day in a quasi-supervisory role, my coworker made a point to offer a reminder (an unnecessary one, in my oh-so-humble opinion) about something I was doing.
I remember thinking, “Dude – we started this job at the same time. We were working side-by-side yesterday. You only got promoted first because you’re older.”
We were 14 and 15, so age really did affect role eligibility.
And at that age…what could I expect? It’s not like the company offered managerial training for 15-year-olds.
If only that limitation were contained to food service jobs staffed by teenagers…
Far too often, talented employees are elevated into leadership roles without anyone sharing the hard truths about what that transition entails.
If your organization is growing, you may be in a position to smooth that leap for new leaders. Heck, you may even find yourself in that transition.
Here are 5 hard truths everyone making the leap into a leadership role would benefit from knowing.
Your Job is Different Now
With a few exceptions, being elevated into a leadership role doesn’t mean doing more of the same job with slightly different parameters.
It means your role has fundamentally shifted – from doing great work, to empowering others to do great work.
Especially in the nonprofit world (or any small business), becoming a leader often means taking on additional, collateral duties.
With greater power comes greater responsibility (to paraphrase Spiderman’s Uncle Ben). And maybe a different schedule. And more accountability for things that used to be someone else’s problem.
This may be the most obvious of the “hard truths,” and yet many newly-promoted individuals are never told precisely how their job will now be different. You can change that trend by being (or asking your supervisor to be) explicit about what will change.
The Skills You Need are Different Now
This truth follows naturally from the preceding one: what got you here won’t get you there.
Your new leadership role requires new skills, ones that likely weren’t part of your previously role if you were an individual contributor: Delegating tasks and managing the workloads of others. Translating big-picture goals and outcomes into assignable tasks. Evaluating performance. Motivating, mentoring, and training others.
These are skills anyone can learn. But it can take time. And it may mean that, for a while, you won’t be great at your job (like you were when you got promoted).
Set your new leaders (or yourself) up for success by getting clear on what skills they (you) will be expected to develop, identifying resources (training, mentorship, coaching) to assist with that development, and showing them (yourself) some grace when they (you) screw up in the beginning.
Delegation Isn’t Optional
Of the leadership-specific skills I mentioned above, delegation is often the one that leaders I coach struggle with the most. It’s often a challenge because new leaders often:
Are used to doing tasks a certain way and don’t trust their teams to meet their standards,
Worry about overloading their team members, and/or
Feel more comfortable handling tasks with which they are already familiar.
Those reasons come from a good place and they may, in some situations, be compelling enough not to delegate. Far more often, however, these truths will tip the scales toward delegation:
Delegation is key to developing your team. They’ll never meet your standards (which, let’s be honest, may need to be recalibrated anyway…) unless you give them the opportunity to learn.
You risk taking on too much yourself. Don’t be a martyr! If you have too much on your plate, and delegating a task would put too much on someone else’s plate, then it’s time to change something about your priorities, your processes, or your expectations. Overwhelming yourself sets a bad example and will prevent you from being the best leader you can be.
Your time is precious. Always consider what use of your time as a leader is the most valuable for the organization. Delegate, outsource, or delay the rest, even if you can do it.
Again, delegating is a skill. Here’s a simple, two-step approach to doing it better.
You Can’t Know Everything
As an individual contributor, it is possible to know everything about the tasks under your purview: what needs to be done, how to do it, the status of every task, what’s working, and what isn’t.
Even if you supervise one other person, you can’t possibly know everything about the work that now falls under your leadership. Things change too quickly and it would be impractical for your team to communicate everything with you.
Likewise, it’s impractical for everyone on your team to know and keep track of everything on your plate.
This is why team building and communication drive effectiveness. You need to trust one another to share what’s important in a timely manner.
As a leader, you can help by setting clear expectations for what you need to know and when, fostering a culture of feedback, cultivating team trust, and proactively sharing the information your team needs.
Your Relationships with Your Peers Will Change
If you were friends with your colleagues before you became your boss, the hard truth is that those relationships will change.
That doesn’t mean you can’t be friends with your coworkers (including those who report to you), but consider:
Setting clear boundaries around behaviors and topics of conversation, in and out of the workplace. For example, gossiping about the organization may have been tolerable (if not a great idea) before, but it risks greater consequences when you’re in leadership.
Clarifying which “hat” you’re wearing in any conversation. Are you approaching someone as a friend, or as their boss? The latter may involve difficult feedback to deliver to someone you’ve considered a peer.
Closely monitoring and adapting for the risk of bias in your leadership decisions. People are highly attuned to perceived unfairness, especially for workplace issues like performance reviews, pay, and role selection.
Whether you’re entering a new phase as a leader or guiding members of your team through that transition, it helps to be honest about how your or their worlds will change. Leadership is hard – don’t go it alone or leave your team members to figure it out own their own. And set a time to talk with me if executive coaching could help you or a member of your team manage the leap to leadership.