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This is that truth. Every week.
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Dear Reader ,
Abere ona ki n ṣina. In Yoruba, this proverb says simply: the one who asks for direction never loses their way.
It is one of those sayings that sounds almost too simple to be profound. And yet it describes, with remarkable precision, the single most common mistake new managers make when they step into a leadership role.
They stop asking.
Not because they are arrogant, not because they do not care but because somewhere in the transition from individual contributor to manager, an assumption has been made.
An assumption that the promotion is a call to fix thing rather than understand them, to lead and not listen, to answer questions and not ask them.
So they walk in ready.
Ready to restructure. Ready to set new standards. Ready to prove that the decision to promote them was the right one. They arrive with solutions to problems they have not yet fully understood, for people they have not yet properly met, inside a system they have not yet taken the time to learn.
And that, more than any skill gap, more than any experience deficit, is where the struggle begins.
The Answers Are Not Going To Come And Find You.
Here is the truth about stepping into a new management role that nobody puts in the offer letter:
The information you need to lead well is not sitting in a dashboard or a handover document. It lives in people. In relationships. In the unwritten rules of a team that existed long before you arrived. In the priorities of stakeholders who have been watching to see what kind of leader you will be.
You cannot observe your way to that information. You cannot assume your way there. You cannot perform your way there. You have to ask your way there.
This is precisely where most new managers get it wrong. They are so focused on being seen as capable that they never stop long enough to become informed. They confuse movement with progress. Activity with understanding. Confidence with clarity.
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The Yoruba proverb does not say the one who knows the way never gets lost. It says the one who asks for direction never gets lost; because knowing is not the point, seeking is.
What The Research Says
This is not just wisdom passed down through generations. Leadership research consistently supports it.
Michael Watkins, in his landmark work on leadership transitions, argues that the single most important thing a new leader can do in their first 90 days is build their understanding before they build their agenda.
He calls it learning before leading, the deliberate, structured process of asking the right people the right questions before making any significant decision.
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Edgar Schein, the organisational psychologist behind Humble Inquiry, goes further.
He argues that the quality of a leader's relationships, and by extension, the quality of their results, is directly determined by their willingness to ask rather than tell.
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In Schein's framework, the most effective leaders are not the ones with the best answers. They are the ones who ask questions that open up information others were not planning to share.
Situational Leadership theory, developed by Hersey and Blanchard, adds another dimension:
...effective leaders diagnose before they prescribe. They assess the readiness and capability of their team before deciding how to lead them. That diagnosis is impossible without asking.
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The evidence is consistent.
The instinct to ask is not a sign of weakness in a new manager. It is the foundation of everything that follows.
So Here Are The Questions You Should be Asking.
This is not just for your boss, but every key stakeholder in your new world. Why, because your success as a manager is not determined by one relationship, it is determined by all of them.
Ask your boss
- What does success look like for me in this role at 30, 60, and 90 days?
- What are the top three priorities for my team right now?
- What should I know about the team's history and dynamics that is not in any document?
- What are the biggest risks or challenges I should be aware of?
- How do you prefer to communicate and how often should we check in?
- What mistakes have you seen other new managers make in this kind of role and what would you want me to avoid?
What you are really asking is: What does my boss need from me and what does winning look like in their eyes?
Ask each member of your team:
- What is working well on this team right now that you would not want me to change?
- What is frustrating or broken that you think needs attention?
- What do you wish the previous manager had done differently?
- What do you need from me specifically to do your best work?
- Is there anything about how you work, your style, your goals, your constraints, that you want me to know?
What you are really asking is: Who are these people, what do they need, and what have they been carrying that nobody has addressed?
Ask your peers:
- How does this team typically work with other departments?
- Are there any relationships I should invest in early, or any tensions I should be aware of?
- How do things really get done around here, beyond the official process?
- What do you wish someone had told you when you first joined this organisation?
What you are really asking is: What is the informal landscape of this organisation and where do I fit into it?
Ask other key stakeholders:
- What does your team need from mine and how well have we been delivering on that?
- How would you describe the relationship between our teams right now?
- What is one thing we could do better or differently that would make your work easier?
- How do you prefer to communicate and how often would you like to hear from me?
What you are really asking is: Who depends on my team, what do they expect, and what do I need to protect or repair?
Finally, Ask yourself:
- What assumptions am I bringing into this role that I have not yet tested?
- What am I avoiding because it feels uncomfortable, and what is the cost of that avoidance?
- Am I moving because I understand — or because I am afraid of being seen standing still?
What you are really asking is: Am I leading from clarity or from anxiety?
On a Final Note
Abẹrẹ ona ki n ṣina. The one who asks for direction never loses their way.
Your first 30 days are not for performance, they are for investigations. A deliberate, structured effort, by you, to understand the system you have just entered, the people, the history, the priorities, the politics, and the unwritten rules, before you begin to shape it.
The managers who get this right do not just survive their first year, they build something that lasts; because their leadership is built on understanding rather than assumption, on insight rather than urgency, on the quiet courage it takes to ask when everything around you is expecting you to answer.
So here's my charge to you. Go and ask. Ask loads of questions. The way forward is in the answers.
A Helpful Resource
The First 90 Days Playbook gives you the complete week-by-week framework for navigating your first 90 days, including the exact conversations to have, the questions to ask, and the decisions to hold off on until you are ready to make them well.
Whether you have just started your journey, you're well in the middle of it, or you are looking forward to starting, this ebook will serve you well.
Still learning
Eyitemi
Founder, The Management Lab