Managing Older Managers: A Guide For Younger Bosses

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You already know that winning depends in no small part on hiring people better than yourself. If you are a youngish entrepreneur or boss, that will entail hiring older and more experienced people, especially in top roles for your organization. Managing a colleague with ten or fifteen more years of experience than you can present unusual challenges of motivation, boundary-setting, and leadership. Here are some ways to get the most out of your hires and your collaboration with them.

Load them up on context. Even more than with other colleagues, you should over-communicate your company vision, industry objectives, and company-wide targets. This should be the number-one focus from the first recruiting day and should remain so for the duration of your relationship. Senior managers, no matter their level of experience, will look to you as the leader to set and communicate the vision. Without it, they will perceive the ship to be rudderless. Remember that the definition of vision is the ability to connect a big goal with the intervening steps required to attain it. You must be able to communicate in broad strokes how the overall objective depends on the performance of each senior manager’s sphere. Ideally, you will make this connection so clear as to communicate that the entire company’s fate is in her hands.

Avoid getting too granular. The excellent senior manager will take it upon herself to apply the context you provide to the mission with which you have charged her. Expect as much, and she will feel respected and fired up. Giving her wide berth to define operating details is the best way to get optimal performance. Ask her to set her own divisional targets or metrics. Inviting a senior manager to do so is an essential trust-building step. You can and should feel free to tweak her draft, but letting her set out the first iteration is a best practice.

Conversely, if you find that one of your senior managers is not performing, the most effective way to communicate that is to tighten your grip on operating metrics and methods. Senior, experienced people like nothing less than having you interfere in their day-to-day work. You should therefore avoid this lever until you can’t, but don’t be afraid of it when it comes time.

Let them know that you are working long and hard. Even accomplished, self-motivated senior colleagues won’t work harder than you will for very long. Send emails early and late. Invite meetings on weekends and at odd hours. Be in the office or online all the time. Dial into meetings at insane hours during overseas travel. Understand that managers older than yourself may have families that require them to live by different rhythms from yours—they may need to be offline from 6 to 8, for example. But expect them to be working long and hard, whenever it is, and make sure you are always doing more than they are. Because you have less natural authority when working with older people, reinforce your “moral right” to demand hard work by showing that you demand even more of yourself.

Show that you are calm in a storm. Good senior managers will follow people they think have good ideas, good judgment, and good cool under pressure. They’re likely to believe that a young, entrepreneurial boss has good ideas, but they may be skeptical that good judgment and calm wits accompany them. If you think you may be prone to anxiety in a pinch, practice whatever Obama-style mind-over-matter Zen control thing you need to do to keep your voice steady, your humor at hand, and your body language relaxed. That doesn’t mean you can’t wake up your team at midnight when the website goes down, the key account blows up, or the factory machine line stops. You should. But keep the coolness and light in your voice when you do.

Seek their opinions, even when you don’t really need them, especially on topics that aren’t within the reach of their roles.


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