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How do you question the boss's plans?

A good leader wants the plan to be right, your next cashier might be on zoom and don't let a sabbatical hurt your chances of a new job

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The Deputy
April 18, 2024

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In today’s email:

  • Job News: How to question the new boss when you just want to win 🏅

  • Overheard at coffee: Did you tip your cashier who greeted you on zoom?... 💁🏼‍♂️

  • Trending AI Tools: Chatslide - All-in-one AI assistant for creating professional slides 😅

  • Hot Jobs: (keep scrolling down ⬇️)

  • Recruiting Fails: Don’t let your sabbatical hit you in the rear end ❌

Job News

The other day a colleague who I have known for 24+ years reached out to me for some career advice. To protect his identity, let’s call him Larry. Larry’s issue was around his new boss.

Backstory, Larry has been a top performing sales representative at his company (healthcare and pharma space) for the past 16 years and has been struggling recently with his new boss. His boss is the VP of Sales and new to the company. 

Larry was reprimanded for questioning the new boss’s strategy. Having known Larry for years and the size of deals and level of passion he has for his profession I can see his words being taken the wrong way. Note to the boss: the last thing you want to do is NOT listen to your top performing sales rep. Side note, Larry sold the company’s first $1B deal. That’s a B for billions and Larry still regularly hits quota and does well.

Too many of us work at places where we don’t dare question the boss. If you are in this spot, you are working for a mediocre leader. A real leader wants to know the truth and doesn’t care who is right. 

There are bosses across corporate America who think their plans are great because they are the boss and few people ever challenge their plans. The good bosses want you to challenge their plans. They want the best plan possible. 

You should care about your job like Larry and be ready to speak up when you disagree with the company plans. You should disagree but suggest a different or better alternative, don’t just complain.

This doesn’t mean you are insubordinate if you question the plans. It means you have a perspective. Be clear with your intent. Are you questioning to get better clarity on the plans OR are you questioning because you don’t believe in the plan? If you don’t believe in the plan, create a better plan with better data to support your plan.

Something tells me Larry will figure out how to partner with his boss and his boss will quickly realize he needs Larry to win. Larry is a veteran and wants to win. 

The problem with Larry and the new boss is Larry’s approach. He needs to work on how he asks the questions. Questions are powerful and should open up a dialogue. 

A good question will engage people’s best thinking to get to the truth of the matter. A good read at The Systems Thinker will help you frame your questions better.

A good question is simple and clear. What are you waiting for? Make something happen.

Overheard at coffee ☕️

Did you tip your cashier who greeted you on zoom?...

An NYC chicken joint has outsourced their cashier job to the Philippines. If you find yourself in Long Island City in New York at Sansan Chicken you may be greeted by Pie, the 33-year-old hostess who works from her living room in the Philippine city of Subic.

Don’t knock it until you try it. The cashier job could soon be replaced by an AI chatbot and if you step into a McDonald’s many of them now have a kiosk with a computer screen that takes your order. You don’t even speak to a human.

We are in the early stages of change with having a cashier on zoom but keep an eye out for something to change in the cashier space. 

I’m all for new technology to make things easier, but sometimes you need to have small talk with the cashier to add some color to your day. 

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Recruiting Fails: Don’t let your sabbatical get in the way of finding your next job. We recently contacted a candidate who was a perfect candidate for a senior level engineering job, but he was on his sabbatical. While sabbaticals are great, the problem is this candidate expected the company to wait to interview him for 30 days until his sabbatical is over…

Sadly, the job will probably be awarded to someone else before he is back. 

The failure here is thinking you are so important that people will wait for you. While sabbaticals are important, finding a job to come back to is equally important. Take a break from your sabbatical for a few hours and interview when you get the chance. The world will NOT stop while you are away in the woods doing ice baths and drinking ayahuasca brew. People are still doing business while you are away. 

We want the sabbatical candidate but it’s hard to present him to a client when he can’t interview with the hiring manager for another 30 days.

If you want a job, you are rarely important enough for a company to wait for you. If you are that important you probably aren’t reading this newsletter. 

* If you are taking a sabbatical or thinking about a sabbatical, HERE is a good read to help you prepare.

Do you have recruiting Fail Stories? Reply with your epic fails – we'll feature them. Own your blunders, embrace vulnerability, and let's all level up together.

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