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Deborah Grayson Riegel Headshot

The One Crucial Conversation Every Manager Should Be Having (But Probably Isn't)

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"All organizations are perfectly designed to get the results they are now getting. If we want different results, we must change the way we do things." -- Management expert Tom Northup

Whether you have a manager, are a manager, or both, you know that on many days, you barely have time to eat lunch -- let alone set a course of organizational change. And when time, energy and resources are limited, we tend to default to the kind of managerial tasks, activities and conversations that we've always engaged in. So it's not surprising that we get the outcomes we've always gotten.

While managers may not have enough autonomy to radically change their tasks and activities (which are often directly dependent on the tasks and activities of their managers) they usually do have enough autonomy to add one new conversation with their direct reports and their own managers to what I call the three "Standard Supervision Conversations":

1) The "How Am I Doing Overall?" Conversation: This is the discussion about what you should be doing, are doing and will be doing, as it compares to past goals and expectations, and aligned with future plans. A subset of this is the "How Am I Doing on this Project?" Conversation, where you get on the same page about progress of a specific project or program that you are working on. Expect to chat about milestones, deadlines, resources and troubleshooting.

2) The "What Do I Need To Learn for this Job?" Conversation: Your job isn't just about applying what you know how to do right now to today's workload. Your manager is charged with talking to you about how you can help grow your knowledge, skills, experience, motivation and confidence to allow you do your job better and support you in taking on new tasks. In addition, any discussions about the new training, coaching, instruction or hands-on experience you take on should include a conversation about how these new skills will also benefit the team and the organization.

3) The "Where Are We Going with All This?" Conversation: This is where you and your supervisor shift the focus from doing and planning to visioning. In this discussion, you'll cover how what you are working on now fits in departmental and organizational plans, where the possible changes and opportunities are, and how to be both responsive and proactive to shifting needs and priorities.

Let's assume that you're having those discussions with your manager or direct reports. Isn't that enough in today's busy workplace? Well, it is enough if you can barely get time on your boss' calendar, or if your annual performance review happens once every year and a half, or once every two years, or...never. It is also enough if your goal is to keep your nose clean and a steady paycheck coming in. But it isn't enough if you subscribe to author Studs Terkel's vision that "work is about a search for daily meaning as well as daily bread, for recognition as well as cash, for astonishment rather than torpor; in short, for a sort of life rather than a Monday through Friday sort of dying." And it certainly isn't enough if you want to yield different results.

So what's the one crucial conversation you need to add?

The "How Are We Doing in Our Relationship?" Conversation: In too many cases, the relationship between the manager and the direct report isn't given attention unless or until there's a problem. And when you wait until it's gotten uncomfortable, threatening or standoffish, that conversation is even more difficult (or impossible) to have. Discussing what you want from your relationship with your boss with your boss is far more effective than kvetching about it over drinks after work with disgruntled colleagues. Whether you're just starting the relationship with your manager, or you've been working together for years, here are ten questions to ask each other that can dramatically improve the dynamic between you, and create the foundation for achieving radically different results.

1) What do you like most/least about working with me?
2) What do you wish I were doing more of/less of?
3) What have you been avoiding telling me?
4) What can I do to make your day?
5) What's one dynamic in our relationship that you really appreciate?
6) What's one dynamic in our relationship that isn't working for you?
7) What do you think we can learn from each other?
8) How should I get your attention about something urgent if other methods haven't worked?
9) What should I never say to you?
10) How do you want to hear feedback from me?