Why Capable Employees Keep Seeking Reassurance
You've got a member of your team who's experienced, knowledgeable and good at what they do. You trust them, you're happy with the quality of their work and you know they're capable of making sensible decisions.
Yet they still seem to need you involved in everything.
You're copied into emails that don't really need your attention. You're asked to check things you know they can handle. They come back for reassurance about decisions they've probably made correctly already.
Over time, it can become frustrating. It adds to your workload, interrupts your day and leaves you wondering why somebody you trust doesn't seem to trust themselves.
It's tempting to think that the answer is simply to ask them to stop.
But what happens if the reason they're seeking reassurance hasn't been understood?
What's really behind the need for reassurance?
There are several reasons why a capable person might repeatedly look for confirmation.
They may be unsure about exactly where their authority begins and ends. They might worry about making the wrong decision or disappointing somebody. Perhaps they've had previous experiences where taking the initiative resulted in criticism, or they've become accustomed to having their work checked.
For some people, confidence in their own judgement can be an issue even when they have plenty of knowledge and experience.
It's also worth considering how the business operates.
Has the owner always been closely involved in decisions? Are people encouraged to take responsibility but expected to keep management informed about every detail? Are expectations clear, or have working habits developed over time without anybody questioning them?
Sometimes it's a combination of the individual's confidence and the environment they're working in.
Even in a business with a supportive leader and an open-door approach, somebody may struggle to recognise their own capabilities or feel comfortable acting independently.
The important thing is to understand what's happening rather than assume you already know.
Why simply telling somebody to stop checking may not help
Imagine an employee who regularly copies their manager into client emails.
The manager knows the employee is perfectly capable of handling those conversations and eventually says, "You don't need to keep copying me into everything."
From the manager's perspective, that's a reasonable request.They're giving the employee more freedom and trying to reduce unnecessary communication.
But what does the employee hear?
If they were copying the manager in because they genuinely thought it was expected, the clarification might be all that's needed.
If they were doing it because they felt uncertain, however, the instruction may leave them feeling even less comfortable.
They may now be worrying about whether they've made the right decision, whether they should have involved their manager or what might happen if something goes wrong.
The visible behaviour might change, while the underlying concern remains.
That doesn't mean managers should accept every request for reassurance indefinitely. It means that how the change is introduced matters.
Start by understanding what the employee needs
A useful starting point is a conversation.
You might ask what prompts the employee to seek confirmation, whether there are particular situations they feel less comfortable handling, or whether they're concerned about making a mistake.
It can also be helpful to clarify what they believe you're expecting from them.
You may discover that the employee has a very different understanding of what needs your involvement.
Perhaps they think you want to be kept informed about everything. Perhaps they've interpreted a previous conversation as a requirement to check certain decisions. Or perhaps they know they're allowed to act independently but still don't feel confident doing so.
Those are different situations, and they may need different responses.
Listening to the employee's perspective can help you decide what support would genuinely be useful.
Create clarity that gives people confidence
Once you understand what's happening, there are some relatively straightforward things you can do.
Agree what they can comfortably handle themselves.
Be specific about the situations, decisions and communications you're happy for them to manage independently.
For example, if someone regularly copies you into routine client correspondence, agree which types of communication they can deal with without involving you.
It's equally important to be clear about the exceptions. There may be particular risks, unusual situations or sensitive client matters where you genuinely do want to be involved.
Make it clear when they should ask for support.
People need to know that asking for help is acceptable, particularly when something falls outside their experience or authority.
You want to encourage confidence without leaving somebody feeling that they have to manage everything alone.
Consider a short, temporary check-in.
For somebody who's become accustomed to keeping you involved in everything, it may help to introduce a brief weekly conversation.
This might be ten or fifteen minutes to discuss anything important they've handled, issues they've encountered or situations they'd like to learn from.
Keep it focused and review whether it's still needed as their confidence develops. The intention is to provide some reassurance while helping them become more comfortable relying on their own judgement.
Some employees won't need this additional step at all. Once expectations are clear, they may be perfectly happy to get on with things.
What is the wider team culture encouraging?
Although the behaviour may be most noticeable in one employee, it's worth considering whether similar patterns appear elsewhere in the business.
Do people feel comfortable making decisions within their roles? Is there a shared understanding of when to involve others? Do managers communicate their expectations consistently?
Think too about whether people receive the same message in practice as they do in conversation.
An owner might genuinely want their team to work more independently but still find themselves stepping into matters that others could manage. Over time, that can make it difficult for employees to judge when they're expected to take responsibility.
These everyday interactions are part of your business culture.
Clarity, Connection, Communication and Cooperation all influence how confidently people can work together.
When those things are working well, there's a better foundation for people to contribute, use their judgement and support one another.
Helping capable people become more confident
Confidence doesn't necessarily develop simply because somebody has more experience or responsibility.
Sometimes people need clearer expectations. Sometimes they need opportunities to practise using their judgement and discover that they can handle situations successfully. Others may benefit from understanding the personal patterns that make them seek reassurance in the first place.
The response needs to fit the person and the circumstances.
If you'd like to understand more about what might be happening from the individual's perspective, I've explored this in my recent newsletter article , Why Reassurance Can Feel Necessary, Even When We Know What We're Doing. It looks at why seeking reassurance can become a familiar response, even when we know we're capable of making the decision ourselves.
As a business owner, you have an important role in creating an environment where people understand what's expected, know when to ask for help and feel supported in developing their confidence.
It's also worth recognising that you may not immediately know what's driving a particular behaviour. Taking time to understand it can help you avoid changes that create more uncertainty.
The next time a capable employee comes back to you for reassurance about something you know they can handle, consider asking yourself:
What might they need to feel more confident handling this without me?
That question could open up a much more useful conversation.
Understanding how your team is really working
Recurring patterns of communication and reassurance can sometimes point towards wider questions about how your team works together.
My Working Together Review provides a structured opportunity to explore your team and culture from the business owner's perspective, understand what may sit beneath recurring frustrations and identify two or three priorities for improvement.
If some of these situations feel familiar in your business, let's arrange a time to talk.
We can explore what's happening, what you would like to change and whether a Working Together Review would be a useful starting point.
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