How to Tell Your Boss He's Wrong

It's surprising how many sales professionals mysteriously lose their ability to sell when they're working on inside issues. A reader writes:

I was recently hired in a sales leadership role, to which I was bringing deep experience. Over the first few weeks, I gathered data and information, which led me to conclude that my territory was doomed to failure (as it had previously failed) if we followed our company's current strategy. Since I reported directly to the CEO, I wrote him a professional report explaining why the current strategy would fail, what should change, and how the firm would benefit from that change, with a detailed cost/benefit analysis. The CEOs response was: "I felt you were criticizing me!" Everything went downhill from there and I was canned. The way I saw it, I had a choice between speaking up and losing my job in three months, or being quiet and losing my job in six. What do you think?

Suppose you had a customer that was doing something stupid and hadn't yet figured out what was wrong. How successful do you think that you'd be selling to that customer if you opened your cycle by sending them a detailed report that said: "You've been doing stupid things, and you've been too stupid to figure that out, and here's what you need to do differently?"

You should have treated your CEO like a customer. Here's how:

STEP 1. Lay the Groundwork. Spend one-on-one time with the boss, finding areas where he is open to new ideas and planting seeds of discontent with the current strategy. Ask questions like: "Why did this strategy fail in the past?" "What other strategies have you considered?" and "What strategy might we pursue if this strategy doesn't pan out?" This is, of course, very basic consultative sales theory.

STEP 2. Offer a Face-saving Alternative. Give the boss an excuse to change strategies without looking like an idiot. Blame changes in the outside world that have suddenly made the current strategy financially impractical, rather accusing the boss of persistent woodenheadedness. Example: "Due to rapidly changing market conditions, our current strategy will require an additional $25 million in marketing to guarantee success."

STEP 3. Transfer Ownership of the New Strategy. Package your new idea as something that the boss created, and which you have subsequently fleshed out into a practical alternative to the current strategy. Example: "As you suggested in our meeting on 6/20, the most viable alternative to our current strategy is... And here are some suggestions for implementing your backup plan..."

STEP 4. Present the Alternative in Person. Because the boss feels ownership of the current strategy, the alternative strategy should be presented face-to-face (or even lips-to-butt), so that you can better sense the boss's reaction and help him make the transition. This is exactly like presenting your solution to a customer and then closing the deal.

Is the above routine more hassle than writing an "I'm right; you're wrong" report and dropping it on the boss's desk like a dead mackerel? Absolutely. But unless you're willing to sell your ideas, you can't expect other people to buy into them.

For future reference, you can get some more detailed information on handling bosses in these feature articles: How to Manage Your Boss and How to Sell an Idea.