I have been a troublemaking, fence-testing employee. I've had a lot of jobs. In my youth, I would find a job that provided some money and an interesting skill or adventure. Of no immediate importance was being a great employee. Usually, I would get hired — and then figure out how to stay just this side of getting fired. 

More than once, on the first day of a job, I would show up late to see if my boss was serious about the start time. If there were no consequences to my tardiness, I knew my boss didn't mean what he said. He had a lapse in integrity. Ouch, right? 

I could use it to my advantage. If I wasn't clear on the rules of the game or the point of any of it, I would play my own game. Like, I wonder if my boss will notice that I'm late? I once worked for a manager who charged his employees $5 every time they were late. What I understood was, I could be late for $5. Sign me up for that one every day! 

Let's explore tough questions, snappy answers and difficult conversations with team members. My troublemaking past has informed me as a leader and manager. It's my job (and yours) to craft a reasonable, compelling game worth playing — and to hold people accountable.  

'What do you want me to do now?' 

In my career, I've visited hundreds of companies. Over and over, I've found that the people at the top of the org chart are buried in work, yet the front-line crew often has time, energy, ideas and expertise. They know what the problems are and how to solve them. And they are under-utilized and unengaged. So, what to do? 

You know I love to ride along or sit side-by-side with team members — it's an opportunity to ask them questions, such as: 

• From your vantage point, what is the most important thing to do every day?
• What gets in the way of doing that?
• What is a waste of your time?
• What can I do to get the rocks out of your road?  

You may want to insist your team members track what they intend to accomplish each day, then back-fill the day with what they actually spent time on. You can use Google calendar for this. The idea isn't to police them. Rather, it's a way to communicate what they are doing versus what they want to or should do to succeed. 

Then, you and they can craft their position descriptions. You can assemble a list of B priority projects and to-dos that can be tackled between A priorities or on a slow day. 

Painful, obvious questions 

These would be "Should I answer the phone?" or "Do you want me to put fuel in the truck?" 

Once upon a time, I went to a presentation by sales and management expert Harry Friedman. He got my attention when he said you might deserve those silly questions because you have established yourself as the Answer Guy.

It starts with you trying to be helpful, but team members quit making decisions before long. Or maybe you come unglued if they don't do things the way you would have done them. If you need to be consulted on every decision, you're going to get some frustrating questions. So, it will take discipline on your part to stop this behavior. 

When confronted with an easily answered question, respond with, "What do you think you should do?" If you really tortured your team members up to this point, you might even say, "What do you think I'm going to tell you?"

Preemptively, operations manuals are where most of the answers come from. So, time spent building those manuals is time well spent. Have team members take the first draft at the procedures — remember, they probably have more time than you — and you can review, edit and bless them. 

Some questions aren't answered in the manuals; we want team members to make decisions. A savvy manager friend of mine uses this language: "Check the manuals. If your question isn't answered there, make a decision. If your decision is grounded in what you think is in the best interests of our customers, team or company, we will back you up — even if you make a mistake. Fair enough?" 

May I remind you that common sense ain't common. Maybe their mommas didn't teach them what your momma taught you. One at a time, turn those questions back to team members and assure them that whatever decision they make, the consequences of that decision will lead them to determine if it was a good or a bad one — or if another decision needs to be made to rectify the first one.

'Can I have a raise?'

Another job I had was working in the rental department of a ski shop. In mid-February, every resort mountain worker starts flirting with burnout. With just a few weeks left before the snow melted, one of my teammates got angry at a customer, mouthed off and got fired. 

I cornered my manager right before the big holiday weekend and said, "I want a raise. How about if you give me $2 more an hour and I will ride out the ski season with you." I knew my manager was desperate and I used it to my advantage. I didn't know how else to get a raise. I saw an opportunity and seized it. 

Has that ever happened to you? Someone leaves for $2 more an hour or crosses the line and gets fired? And there you are, all vulnerable and panicky, and one of your remaining team members squeezes you for a raise. 

So, how do you respond to this situation in a more powerful, positive way? Your team members are not wrong for capitalizing on your inadequacies. It's perfectly legitimate for them to ask for a raise if you have not given them any other vehicle for getting one. 

 What if you responded like this: "Let's get you a raise. When you started here, we reviewed the organizational chart. For each position on it, there is a wage. In some cases, there is a potential bonus or commission. Where are you now? What needs to happen for you to achieve the next pay increase?" 

However, it requires you to have all that structure in place. Work with team members to map out the ladder of opportunity at your company. Define the milestones one could achieve to lead him or her to the next rung on the ladder. 

For example, the path from apprentice to Level 1 tech could look like this: 

• Completion of the orientation checklist.
• NATE certification.
• OSHA 10 certification.
• Checklist for software and device (phone, tablet) setup and use. 
• Ride-along and sign-off by a field supervisor of the five most common tasks in the price book.
• Must be an apprentice for at least four months.

Feel free to customize this list, of course — but be sure to keep it objective and behavioral. 

Tough questions? Silly questions? Difficult conversations? Help your crew ask and answer them for themselves. 

By the way, as a young troublemaker, I would test my bosses. Those who held to standards and systems got my attention, compliance, respect and best work. Just sayin'.