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The Questions That All First-Time Managers Should Ask Themselves

If you’ve stumbled into a management position, ask yourself these questions to become the type of boss you’ve always wanted to be.

The Questions That All First-Time Managers Should Ask Themselves
[Photo: Flickr user Khánh Hmoong]

Many of us become managers somewhat accidentally. We need someone to help with work, make a hire, and all of a sudden, we’re managers. Sound familiar?

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In 2008 I inherited my nonprofit’s annual fundraising gala when the person who had been leading it left. When I convinced my Executive Director to let me bring on an event planner to assist, I also became a manager of this person.

Bouree (the event planner) was very competent and experienced, knew the nuances of nonprofit event planning and was (and still is!) delightful–she was the best partner I could have asked for. Yet, it didn’t strike me until the day I sat across from her in our first meeting that it would take a lot of time and effort on my part for the relationship to work and to set her up for success. Getting her to say “yes” to the project suddenly felt like the easy part.

Here are three questions to answer as you prepare to be that purposeful manager you want to be (and what could be at stake if you don’t).

Question #1 is about you: Do you have the time to be a purposeful manager?

The quick answer may be: “No. I don’t have any time. That’s why I need to hire someone!”

Here’s the thing: Even if you hire the most qualified candidate, they will need time to get their bearings in their new role and new organization. (Here’s a plan for the first 100 days.) The best thing you can do to be a purposeful manager is commit to scheduling and keeping regular check in meetings with your people. Meetings might be more frequent as you begin to work together–maybe once a week for an hour when you spend time talking about the work and talking about them and how they’re doing–or even a quick one at the start of each day to set priorities and answer questions.

Check-ins answer questions and remove blocks that impede productive work. It will take time to do them, but far less time that it will take you to fix incorrect work once it’s already done. Plus, you will have happier, contributing and more productive employees, which is good for everyone.

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When I hired Bouree, I could not expect her to just know what I needed her to do (more on that below). We had to set aside the time to meet so I could introduce her to the project and the organization, give her the history of the event and talk through all the moving parts for a successful gala. This took time out of my days up front to get her set up, but in the long run did end up creating more time for me in my schedule.

An accidental manager is someone who doesn’t schedule check-ins, cancels check-ins when something else comes up, or prioritizes their work over their people. As a manager, a large chunk of your work is your people.

Canceling, forgetting or rescheduling meetings sends strong messages. Simply, it doesn’t feel good or show that you care. If it happens a lot, your people could quit. Then you have to take the time (which you already don’t have) to hire someone else or you’re stuck with the work again.

In one role where I managed several people and spent significant time in meetings, I had to find a way to also get work done. What worked for me was blocking my calendar every day in the morning. I let my staff know I would take zero meetings before 10:00am. It allowed me to respond to emails and prep for the day and also be present with my team for the rest of the day in meetings and check ins.

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Other questions about you to consider:

  • What are my expectations as a manager? What are my dealbreakers?
  • What is my management style?
  • How do I like to be communicated with? (Are text messages okay to let you know I’m running late? Will we be friends on Facebook?)
  • How flexible am I? (Is it okay for me to work from home sometimes? Can I come to work around 9:00am or by 9:00am every day? Can I take a late lunch to go to an appointment?)
  • What do I want my people to say about me (If you want them to say you are there for them and a good listener–do those things!)

Question #2 is about the work: What does success look like?

Simply said: What do you want this person to do?

With Bouree on the team to help with the gala, there were any number of things she could have helped with given her experience. As we talked about all the moving parts, it became clear she should hold specific pieces. Since she wasn’t a staff member with the organization, it didn’t make sense for her to solicit for sponsorships or speak to our staff about the event. Because she didn’t know in depth about the services we delivered, she was not in charge of crafting the event program.

We got very clear on what her work was and by when it needed to be done. When we met regularly, we were able to check in on the specific work she was responsible for and her progress. We also talked about any challenges, questions or resources she needed or barriers to the work so she could do what was expected of her.

It is the job of the purposeful manager to define what the work is. A clearly written position description is the best way to start (and will also help you get the right person, more on that below). The position description is a primary source for developing goals and areas of focus for your new staff person and is a good reference document for performance reviews.

An accidental manager may hire someone without a fleshed out position description and will speak vaguely about responsibilities. This will create confusion and may result in your staff focusing on work that is not the priority or doing work incorrectly, ultimately creating more work for you that will take additional time (that you don’t have).

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“Don’t make ‘em guess” is a piece of advice I was given years ago about leading people. It is the job of the manager to spend the time upfront getting clear about what the work is, what success looks like and communicating and checking in frequently to ensure your expectations are clear and being met. This structure and clarity will ultimately help staff feel empowered and ownership over the work.

Other questions about the work to consider:

  • Am I giving the right work away? (Can it only be done by you, or is work that you would rather be doing?)
  • How much work is there? (Do I really need someone or could some smart reorganization do the trick?)
  • Is a staff person what I need or could an intern or volunteer fill this role?

Question #3 is about them: Do you have the right person?

This is someone you will be spending a minimum of 2,000 hours a year with–this is 25% of the hours in an entire year! Of course you need them to be able to do the job, but do you get along? Can you imagine working late with them, going to lunch, or being stuck in traffic together?

With a commitment to make the time and getting clear about the work, the question is now–do you have the right person, or the discipline to find the right one?

No matter how talented Bouree was, if she and I didn’t get along and enjoy working together, our partnership would not have been successful. In that first meeting, I was honest with her about the project, what worked and what didn’t in years past and what I needed her help with. I had to get a little vulnerable and be honest with her, letting her know that I didn’t have all the answers and needed help. Once we were on the same team and on the same side of the problem, we could begin to build trust and work together on planning a dynamite gala. It took me going first. Don’t be afraid to go first.

An accidental manager might rush through the process, focusing on getting someone in the role as soon as possible so they can offload a bunch of work, never paying attention to fit, interests, and needs. As the purposeful manager, take the time during the interview process to get to know candidates, not just as a worker but as a person. As part of an interview process, I recently heard of one company taking candidates out to lunch, which in a more relaxed environment can tell you a lot about how a person interacts with others and as part of a group.

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Nancy Lublin of DoSomething.org talks about this quite a bit in her video on three rules to hiring.

Other questions about them to consider:

  • What kind of strengths does the ideal person need and is this person it? (This will become evident through crafting a position description. Be careful not to get too caught up and hire a great person without the chops you need.)
  • How do they fit with the organization’s culture? (Are they comfortable in a quiet work environment, working at their desk all day or participating in weekly game of office charades? Be honest and upfront with them about what your organization’s culture is like so they can be honest with you.)
  • What sort of compliment do you need? (Maybe you’re not good with the details or doing the intense research you need. If you need this, hire for it!)

If you are wondering if you are being a purposeful manager, that’s a good sign. That means you care and want to make sure you and your direct report succeed. Remember that no one is perfect, you are a human being and will make mistakes. It’s okay and it’s never too late to hit the reset button and recover.

This article originally appeared on Idealist Careers and is reprinted with permission.