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6 Easy Steps to Holding Crucial Conversation with Your Boss

As a leadership style, micromanagement is typically not only ineffective, but also detrimental to the performance of their team. While getting more involved might make bosses feel more in control, sooner or later, their direct reports will start to feel untrusted, undermined and resentful. When productivity and morale begin to suffer under the strain of micromanagement, cycles of frustration and distrust can hinder good work on both sides of the manager-employee relationship.

The pandemic has had adverse effects on managerial relationships, micromanaging, and communication, according to new research from Blind.

The report found 42% of professionals were micromanaged more during work from home, compared to when they worked in the office. When asked what effect the pandemic had on the relationship with their boss, more than half of professionals (54%) say the pandemic had a negative impact on their relationship.

This is an alarming sign!

Too often people make the trade-off between saying something to their manager and simply stuffing their concerns for fear of being disrespectful or even out of line. But what you need to realise is that silence isn’t noble, it’s destructive. One of the most important principles taught in Crucial Conversations is that what you don’t talk out, you’ll act out.

"If leaders aren't prepared to manage remote teams, or if these teams don't have good communication and collaboration habits in place, the effects of this virus could disrupt team connectivity, morale and accountability—not to mention results,"

– Justin Hale, Master Trainer at Crucial Learning

Over time, your resentment about your concerns about your manager’s behaviour will grow unmanageable. Inevitably, your frustration will manifest itself in ugly vent sessions, backbiting, and gossiping to teammates, friends, family, and anyone who will listen. I also find unresolved and unspoken concerns are at the root of most passive-aggressive behaviour. And, if, by some miracle, this toxic behaviour stays hidden from your manager, ultimately it will cause you to disengage from your role.

The only way forward is to speak with your manager about your concerns. And it is possible to be both candid and respectful with anyone—regardless of power, position, or authority—another tenet of Crucial Conversations.

6 Steps to Holding Crucial Conversation with Your Boss


1. Work On Yourself First, The Manager Second

Before you have a Crucial Conversation, get your emotions in check by looking for ways in which you add to the problem. It isn’t that your manager doesn’t have faults; it’s that we tend to exaggerate the role others play when problems affect us. Honestly examine your own behaviour to see whether and how you might be contributing. For example, you admit to withholding information from your manager. I believe this behaviour is contributing to a vicious cycle: your manager doesn’t receive the communication they need so they micromanage or overstep boundaries, which bothers you, so you withhold information. And so on.

2. Start With Good Intentions

Ask for permission to talk about a concern in private. Once you sit down, thank your supervisor for taking the time. The first thirty seconds set the tone for the rest of the conversation. Explain your desire to work through a problem in a way that meets both of your needs. This win-win tactic may seem obvious, but many people enter conversations with the goal to improve only their own situation—not a good starting point.

3. Focus On The One Issue You Care About Most

While it’ll be hard, avoid airing all these gripes in your first conversation. Instead, work on one issue at a time. Give them time to digest, respond to, and work on your concerns before starting with another issue. This will require careful analysis of what issue is most urgent or problematic. To narrow the field, consider what you really want for yourself, for your manager, and for the relationship. For example, if what you want most is a relationship of trust, address the pattern of micromanagement and wait till that’s resolved before tackling communication boundaries.

4. Stick To The Important Facts

Describe the problem you’re experiencing by starting with the facts. For example, perhaps they asked you to complete an assignment and proceeded to ask for updates several times a day. This is a fact. You may feel they think you’re incompetent or don’t trust you, but these are conclusions. Conclusions are often inflammatory, can be wrong, and frequently create defensiveness. So, start with the facts. What specific actions led you to your conclusions?

5. Suggest Replacement Behaviours

After you’ve explained the problem, suggest what you’d prefer. “It would work better for me if we could check in on the project every other day instead of several times a day. At the current rate, I’m not able to stay focused or create quality work for fear you’ll be interrupting me at any moment.” Often, people behave poorly because they don’t see alternatives. Give them alternatives. If necessary, jointly brainstorm until you come up with a strategy you can both support. One idea: commit to sending a project report every 48 hours detailing what’s been done, what’s in progress, and what is on deck. This may be enough to stop the micromanagement altogether.

6. Define “Who Does What By When” And Express Your Thanks

Wind down by describing exactly what each of you will do to help improve your working relationship. And finish by expressing your appreciation for their willingness to listen to your concerns.

See how this approach is both candid and respectful? You respect your supervisor’s schedule by asking for time to talk when it’s convenient. You respect their reputation and privacy by sharing your concern discreetly rather than in front of the team. You assume the best of them by checking your emotions and story to find where you are contributing to the problem. And you thank them for taking the time to consider how you can work better together. Nothing about this approach should come off as disrespectful. It can also be used with anyone, not just your supervisor.

With the right skills, it’s possible to approach anyone with any title. If they refuse to accept your skilful and thoughtful conversation, that’s their choice, and you may end up where you would have had you remained silent—disengaged and looking elsewhere. However, if you follow the steps I’ve outlined above, at least you’ll know it’s not for lack of trying to improve the situation. And really, that’s all you can do.

Master the skills to deal with high-stakes conversations.

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