Part 1 – Why One-on-Ones Are Where Situational Leadership Happens

This is the first in a three-part series on one-on-ones and situational leadership. In this series, we will share how to use structured one-on-one conversations to tune in to each individual’s needs, customize your management approach, and get better results from every person you manage.

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Most managers develop a style over time. They get into a rhythm. They do what feels natural. They lead, manage, and supervise as they have learned to do through habit, observation, and experience.

The problem is that habits feel right, whether good or bad. Suboptimal habits can feel just as comfortable as good ones.

That is why so many managers default to managing by touching base and interruption. Something pops into your head, so you interrupt your direct report. Something pops into their head, so they interrupt you. The most substantive conversations often don’t happen until something has already gone wrong.

That is not strong management. That is management on autopilot.

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Every person you manage is a special case

Situational leadership does not mean catering to everyone’s whims. It means figuring out what actually works with each person.

Every person you manage is different. What one person needs from you may be very different from what another person needs. What you need from one person may be very different from what you need from another.

It depends on who the person is. It depends on the role they are playing. It depends on the work they are doing right now. It depends on whether they are having a good day or a bad day, a good week or a bad week, a good month or a bad month.

That is why one-on-ones are where all the action is.

Team huddles are important. Documentation is important. High-structure, high-substance communication is always better than low-structure, low-substance communication. But the one-on-one is where you can customize the conversation.

One-on-ones should not be generic check-ins

The three most common questions managers ask are:

• How’s everything going?
• Is everything on track?
• Any problems I should know about?

Those questions do not tell you enough.

They are touch-base questions. They are the questions managers ask when they want to keep the conversation brief and simple. But if the goal is to manage, coach, support, and improve performance, you have to go deeper.

Better questions sound like this:

• What did you do?
• How did you do it?
• What are you going to do next?
• How are you going to do it?
• What is your plan?
• What steps are you going to follow?
• Show me.

“Show me” may be one of the most powerful management phrases there is.

Show me your plan. Show me your schedule. Show me your to-do list. Show me the standard operating procedure you are following. Show me what you have done so far.

The more concrete the conversation, the more useful it becomes.

Structure is what makes customization possible

Some managers hear “customize your approach” and think that means every conversation has to be improvised. Actually, the opposite is true.

The more structure you have, the easier it is to customize.

A strong one-on-one should be regular, planned, and substantive. Both people should prepare. There should be a clear agenda. There should be notes. There should be follow-up. The conversation should focus on the work: expectations, priorities, performance, problems, next steps, and what each person needs from the other.

But within that structure, every person needs something different.

Some people need more direction. Some need more questions. Some need encouragement. Some need step-by-step instructions. Some need help making a plan. Some need help getting started. Some need to be left with more ownership, but not left alone.

That is the art of situational leadership: not changing the fundamentals, but changing how you apply them with each person.

Start by taking it one person at a time

The first step is to stop thinking about “my team” as one single management challenge.

Start thinking one person at a time.

1. Who is this person at work? What work are they doing? What are their top priorities? How are they performing when it comes to attitude, productivity, quality, and self-management?
2. Why do you need to talk with this person right now? What is your goal with them? What do they need from you? What do you need from them?
3. What is your message? What questions should you be asking?
4. How should you talk with this person? Should you ask questions? Give instructions? Review a checklist? Help them make a plan?
5. Where should the conversation happen? In person? On the phone? On video? In a place where they can show you the work?
6. When should you talk, and how often?

Those six questions — who, why, what, how, where, and when — are the foundation of a simple but powerful tool I call the people list. I’ll dig into that tool in the next post.

Don’t wait until something goes wrong

Too many managers wait until there is a problem before they have a real management conversation. The best one-on-ones are not problem-solving sessions after the fact. They are where you prevent problems, clarify expectations, provide support, and help people improve one step at a time. That is where real leadership happens: in the routine conversations, before anything goes right, wrong, or average. If you want to be a stronger manager, don’t start with a new style. Start with a better habit.

Have regular, structured, high-substance one-on-ones. Then use those conversations to tune in to each person, one at a time. That is situational leadership in action.