advice/perspective on jobs, work and management

Ask for help, or you’re fired

I own and operate a small independent recording company. It’s my dream job. No 9-to-5 grind, I get to work with creative and interesting people, and I’m my own boss. What could be better?

            Recently I hired someone at the “director”-level (I’m not a big fan of titles), and so far it’s not working out. I’d hoped he’d be able to start taking projects immediately, but instead I’m finding he needs a lot of supervision. That’s not a big deal in itself; I’m happy to coach/mentor him. The problem is he refuses to ask for assistance when he needs it. As result, I sometimes don’t find out he’s struggling until it’s almost too late (we’ve had a couple of close calls). I’ve explained all this to him, and he insists he’s comfortable approaching me, but it keeps happening. What I really want to do now is sit him down and tell him if things don’t change, I may have to fire him. I’d prefer not to, but things can’t go on as they are. How should I handle this? – Name withheld

You’re in a tough spot.

You have an employee who’s needs support, and although you’re happy to give it, you can’t convince him to seek you out when he does.

Take comfort in the fact that your experience is not unusual. Nor is it unique to your organization. What you’re dealing with is one of the oldest, and most vexing dilemmas in all of management.

Let’s call it the “Advisor-Evaluator paradox.” Simply put, it means that as a manager, you have been assigned two very different, and ultimately incompatible­ roles.

The first is that of advisor.

As you clearly recognize, one of your primary responsibilities as a manager is to support your employees in their work so that they might do their jobs to the best of their ability. This could mean offering advice/guidance when asked, or encouragement when your employees seem unsure of themselves. Or, you may even need to gently tell them what to do if they’re about to make a mistake.

The other role you assume is that of evaluator.

As owner and sole proprietor of your business, you are also responsible for its success and financial well-being, as I am sure you are also well aware. It is therefore incumbent upon you (or someone) to monitor the performance of your workers and in that way ensure their work is being done on time, and in a satisfactory manner.

The problem is the conflict of interest these two roles create. What you might learn while acting as “advisor” you could use later against that same employee when acting as “evaluator.”

Say, for instance, your new director lets slip some professional shortcoming while asking you for help, perhaps something you were not yet aware of. What’s to stop you from using this information later when assessing his performance, deciding whether to give him a raise, or making some other organizational decision which affects him? As organizational steward, it would seem all but impossible for you not to take that information into account.

No wonder your new director is hesitant to approach you.

Harvard Professor of Business Administration Linda Hill describes the conflict between the roles of advisor and evaluator as “an age-old dilemma.”[1] Certainly pioneering organizational theorist and author of The Human Side of Enterprise Douglas McGregor was aware of the problem back in the 1960s. “The role of judge and the role of counselor,” he wrote in his now classic text, “are incompatible.”[2]

So what can you do to get your new hire to open up?

Well, unless your willing to relinquish one of these two responsibilities (I’ll let you decide which one), you will never be able to put your employee’s mind totally at ease.[3]

What you can do, however, is help him forget about your evaluator responsibilities to the extent that’s possible. Be as supportive as you can in your interactions with him. Proactively ask if he needs help, then be especially understanding when he does. And finally, remind him that it’s not really you who’s evaluating his performance. It’s your clients. Insist that as long as they’re happy, you’ll be happy…which hopefully isn’t too far from the truth.

Keep in mind too that this individual’s previous employer(s) may have put a high value on “self-starters” capable of working independently, and who can power through difficulties on their own. Current business culture certainly does.

His failure to approach you for help is probably not a sign of incompetence, in other words. Nor is he deliberately trying to make your life difficult, I’d wager.

In fact, if I had to guess, I’d say he’s trying to impress you.



[1] Hill, Linda. Becoming a Manager. 2003. (Boston, MA: Harvard Business School Press), p. 209.

[2] McGregor, Douglas. The Human Side of Enterprise – Annotated Edition. 2006. (New York: McGraw-Hill), p. 117. Originally published in 1960.

[3] Interestingly, one organization that has successfully resolved this paradox is the government. Specifically, the criminal justice system. Attorney-client privilege, Miranda rights, the presumption of innocence, trial by jury – all are intended to keep the roles of advisor and evaluator separate and distinct, and thus ensure the fairest possible treatment under the law. Indeed, one can only imagine the sort of justice that might result if the arresting officer, attorney for the prosecution, defense attorney, judge and jury were all the same person.


  1. Tim Eiler

    Speaking as a manager/leader of staff, this conundrum is definitely valid. Your answer was also spot on, in my opinion, while somewhat simplified and non-specific.

    Speaking as an employee of an organization, damn straight that it’s a fine line to find and walk between “be a self-starter, solve problems on one’s own, and don’t ‘bother’ the boss with trivial problems” and ask for help. I’m really glad you pointed out that dilemma! From the employee’s side, I think the only way to resolve it involves (a) talking proactively with the manager about the situation and trying to “find the line” and (b) eventually finding the edges of the acceptable envelope. That takes trust – from the employee to the manager and vice versa.

  2. Sandy Kessler

    This post would be a great icebreaker / conversation starter for an employee / manager duo facing this dilemma.

    As you insightfully point out, one of the things that can make this dynamic so challenging is you could very well have 2 individuals approaching the issue with 2 very different (opposite) perspectives. And then, possibly trying to meet what they mistakenly perceive to be their boss’ / employee’s view on asking for help & then adjusting their OWN behavior to fit what they feel helps the other party.

    So then you have 2 talented, well-intentioned people misreading the whole situation. All due to a lack of open communication about what actually isn’t really that sensitive an issue – whether it’s ok / encouraged to ask for help or not. Having an open convo in a non-threatening way at a time when the issue isn’t present could help a lot 🤷🏻‍♂️


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