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Howard Tullman
We’ve all been there, working for someone who seems particularly clueless. But you’re not helpless. A user’s guide to managing your incompetent manager.

4-Jun-24 – It’s more critical than ever these days – in the work-from-wherever environment – to make sure that even if you’re out of sight, you’re never out of mind. Because it’s still a “what have you done for me lately?” world.

No one else is going to tell your story for you or as well as you can, but you need to make sure your message gets through the noise and reaches the right people. And it’s equally important to regularly demonstrate to those folks just how much you appreciate and respect the “enormous contribution” the higher-ups make every day to the company’s well-being and success – even if you sometimes nearly gag as you dutifully spout that pathetic pablum.

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But there’s nothing more crucial than doing whatever you can – aside from the sycophantic strokes and counterfeit compliments – to help make your boss successful.

And there’s no greater challenge today than trying to work with a boss who resents, fears, devalues, or worse yet, simply doesn’t understand or appreciate the need for the new tools and technologies that every business will have to employ in order to remain competitive in the digital future.

While some of the older executives in any business are simply so set in their ways that they’re unwilling and thus unable to learn anything new, the more typical case – especially in tech-centric businesses, and which companies aren’t these days? – is that you’re going to be dealing with someone (a) who’d rather die than die of embarrassment; (b) who’s not so much afraid of change as afraid of looking stupid; and (c) who worries that many of the personal skills and talents that have been developed over decades are going to become less useful, devalued, and even impediments to future growth.

The rate at which someone senior can learn new things is directly proportional to his or her tolerance for embarrassment.

This isn’t simply an age or maturity problem. To some degree we all fear the unknown and anything that we don’t understand. We all care about what other people are going to think of us and don’t want to be humiliated. And we all realize that while we’re increasingly dependent on technology, we have less and less control over where it’s likely to take us. Effective change isn’t driven by fearless champions; it’s driven by thoughtful and persistent strivers who resist and master their fears and keep moving forward.

So, if you’re stuck or saddled with a boss who simply doesn’t get it, and there’s no way around the problem, you’re going to have to develop a plan to deal with the situation.

Sadly, every case is different because of the personalities involved, relative experience and technical backgrounds, and other material considerations. But some things never change and, from a psychological perspective, there are four basic ideas to keep in mind when you undertake one of these thankless and painful tasks.

1 First and foremost, be straightforward about what you’re trying to accomplish, how you hope to pull it off, and why it’s important for all concerned.

It’s hard to be completely open upfront, but it pays off and makes things much easier and more successful in the long run. Strong relationships aren’t supposed to be easy anyway; they’re supposed to be frank and honest.

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Two-way trust is critical because the educational process – explanation, demonstration, correction, and repetition – requires a willingness on the boss’s part to be vulnerable, the ability to accept constructive criticism, and a sincere desire and commitment to learn and apply new concepts and ideas for the ultimate benefit of the business.

2 Set modest and realistic goals for the process, develop manageable timeframes, and agree upon simple shared milestones. Remember that the main objective is not to create the next rocket scientist for the team, but to provide a basic structure and technical framework within which to organize the new ideas and concepts; build some conceptual understanding of how the new technologies work without getting into the weeds; and offer current examples and analogies to existing methods and processes to help bridge the gaps to the future solutions. One good example is worth a thousand theoretical explanations.

3 Understand that enormous patience on everyone’s part will be an important part of the process. Don’t try to get to heaven overnight or cross the chasm in a single bound. There may be delays and early failures, there will certainly be personal concerns and issues as you progress, and there will be aggravating and frustrating interruptions as well, but the saving grace is that most successful bosses are, by definition, resilient and adaptive and understand that the route is rarely straight and free of bumps.

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Time, in this rare instance, is actually on your side because you’re trying to build a long-term advisory connection and, at the same time, walk a fine line between boss and buddy and between control and criticism.

No one – especially leaders – likes to give up control and while everyone occasionally asks for criticism, the truth is that they’re only looking for praise. It’s not difficult to find holes, errors, or faults in someone’s attempts to learn novel and challenging concepts; the difficult trick is to build on what they have learned, to fill the gaps and mend the holes, and to avoid embarrassing or frustrating them so they abandon the effort entirely. It’s not a test or a trial; it’s a joint investment of time and trouble in order to eventually get to a better place.

Finally, you can control the outcome and assure a favorable result – however modest and fleeting it may be – because the person who controls the definition of a problem (or situation) also ultimately controls the solution. If you’re solid and steady in your work, if you ignore the comments and opinions of others who aren’t involved and invested in the result, if you establish some simple metrics, and if you set a firm end date to the process, you alone get the honor and privilege of declaring victory.

At the end of the day, it’s not simply what the boss has learned that matters, it’s what he or she has learned about you, and about learning, in the process that’s the real name of the game.