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Les McKeown's Predictable Success Blog

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5 Ways to Survive a Terrible Boss 

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A version of this article first appeared in Inc.com

There’s nothing more debilitating than heading into work every day depressed at the thought of having to face your dysfunctional boss. 

Founders, in particular, have a tendency to have eccentric personalities – not exactly winning the No. 1 Boss award. The good news is it doesn’t have to be this way. Here’s a five-step plan to survive and thrive even the most malevolent manager:

1. Decide if it’s bad enough to leave.

It’s one thing to struggle with a bad boss. It’s a whole other circle of hell to be stuck in a mire of unhappy, dithering uncertainty about what to do about it.

The first step to recovery is to make a fundamental decision – are you going to stay, or go?

Of course there are a lot of variables involved in making such an important decision – the financial impact, timing, availability of options, for example. But here’s a simple rule of thumb: If issues with your boss run so deep as to be all-consuming, it’s probably time to move on.

2. If you’re staying, stay positive. 

Assuming your boss issues are painful but not all-consuming, it may well be possible to stay and carve out a perfectly acceptable working environment, but only if you build on the right foundation.

That foundation is your personal contentment. If you’re coming to work every day frustrated, discontent, unhappy, then the possibility is slim that you’ll succeed in building a positive environment in which to work.

So if you’ve made a decision to stay, make a conscious commitment to staying positive. Don’t dwell on the things your boss does that infuriate you, and don’t take part in any of the office negativity surrounding your boss’s jerkiness. (Hint: If you find it impossible to maintain a positive attitude, revisit point one above.)

3. Find what develops trust. 

Here’s the key to building a positive environment with any boss, however incompetent or annoying: Unless they’re an outright sociopath, there will be some way, some basis, some process to earn their trust.

The way to build trust with a jerk boss may not be necessarily attractive or becoming. Perhaps you have to watch them take all the credit for what you do, or let them treat you as their personal assistant, or listen patiently to their constant self-aggrandizing storytelling.

Whatever it is, so long as it’s not evil, wrong or demeaning, your job is to identify it, and being bluntly mercenary, use it to build your boss’s trust. (If what your boss expects from you is evil, wrong or demeaning – or worse, they are in fact a sociopath, with no way to build trust – then again, go back and review your decision in point one above.) 

4. Build autonomy based on trust. 

Having built a “trust bank” with your toxic boss, the next step is to trade that currency for something much more useful to you – autonomy.

Use well-placed questions like “Why don’t I chair the Wednesday afternoon meeting so you can accept that golf invitation?“, for example, or “Shall I work on the new product launch over the summer months – I know you have a lot of family commitments then?” to unlock little pools of independence.

Start small. Don’t spook your boss, and use the first few initiatives to build even more trust – deliver on time, and above all, don’t spring any negative ‘surprises’ if you can avoid it.

5. Stay under the radar.

Now you’re off and running. You have your boss’s trust and growing autonomy. The key now is to establish boundaries that will keep you happy and fulfilled without triggering a backlash from your toxic boss. Let the answer to point three above be your guide. If it builds trust, do it. If it doesn’t, beware.


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