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Questions All Leaders Should Ask Themselves

Achieving Goals, Burnout, Career Enrichment, Leadership Coaching
07/24/23 - Nicole Wood
woman working a desk in front of laptop thinking

As leaders, we are time constrained to the max. We are making sure our direct reports have what they need, our superiors or peers have insight to our work, all while trying to get something on our own checklist accomplished here and there. It’s easy to go go go and forget to pause and reflect.

The risk of this is, without taking the time to reflect and question our actions, we can find that we’ve run a million miles an hour in the wrong direction. Or that the direction was right but we missed something or someone along the way.

These 5 questions are critical for leaders to be regularly asking themselves to help ensure their time is well spent, their team is well aligned and their wellbeing is taken care of.

What can only I do?

Leader or not, we are all wrestling with a never ending challenge to prioritize our time and activities. Especially in small companies, you may find yourself doing things, not because they make sense for you to do, but because there is simply no one else to do them. It’s easy to get sucked into stuff because there is a need, but without putting those asks through some sort of filter, they can quickly consume all of your time, leaving nothing left for your priorities.

Ask yourself, “What can only I do?” What are the things that you uniquely have knowledge, relationships or expertise around? These are the things you need to prioritize. Which also means you’ll need to figure out how to delegate or let go of some others. It can be difficult to let something slip that ought to be done. But if those things collectively are preventing you from doing the things that need to be done by you, they’ve got to go.

Does everyone know the one big thing?

At any given point in a business, there is a major headline. It might be a focus on preparing to go public. It might be a season of cost-cutting and profitability. It might be building brand awareness at just about any cost.

Regardless of which team you lead, your team should know the headline. Everyone should know the “one big thing” and how their work contributes to it. If you ask three people on your team, they should say the same thing. And they should have a general sense of how well that thing is going. If they aren’t sure, and especially if you aren’t sure, it’s a great time to refocus on the key priority and ensure your communication is clear and repeated regularly.

Who needs attention?

Especially in a remote or hybrid environment, it can be difficult to sense when someone on your team is struggling. And if it’s not top of mind to be checking in and considering who might need support, your team members could be feeling alone on an island.

Regularly ask yourself who on your team needs attention. Attention might mean recognition. It might mean a chance to grow in a new way if they’ve been doing the same thing for quite some time. It might be reassurance that they are doing a good job, even in the face of challenges. It might mean some additional hand-holding and feedback if they are falling short. Make sure you have regular one-on-ones and pulse check with your direct reports on these categories.

While not with the same intensity, consider how you can support those who report into your direct reports. Skip levels can be powerful both to help you support your managers but also to motivate those below them. You might be surprised at how much a quick 30-minute meeting or pulling someone into a project can do to drive engagement and excitement for the work.

What am I missing?

This is tricky because in most cases, if there was something else to be done to move the business forward, we would have done it already! It’s not easy to see your blind spots personally and strategically.

Challenge yourself with even deeper questions about what you might be missing. What’s happening outside our 4 walls in the world or industry that might impact us in the near future? What have I been so sure about that I’ve forgotten to pressure test my assumptions? What have we been doing simply because that’s what’s always been done?

When trying to push initiatives or results forward, our temptation is often to apply more pressure, to put more fuel on the fire rather than take a step back to determine where we can remove friction. Could that be more impactful? Is there a different approach altogether? Even just taking this brief moment to challenge your work and assumptions and consider what you might be missing can unlock a new burst of genius.

How am I taking care of myself?

Leadership can be a lonely job. It can feel isolating to keep a team of people motivated and engaged when facing difficult or uncertain times. It can be exhausting to not just drive work and initiatives forward, but to be responsible for people’s emotions and the team morale as well. Make sure you are taking care of you. Ask yourself, “What do I need?” That might mean being in community with other leaders. It might mean seeking support from a coach or therapist. It might mean some time off. All of these options require time and investment, but we know that without prioritizing your wellbeing along with your work, burnout is sure to follow.

Take the time to pause and ask these key questions. Better yet, build it into a habit like something you do on your train ride to work or something you do every Friday as you wrap up the week. Systematize your reflection so it becomes part of your work routine. I promise, you’ll never regret taking the time to stop and question. A brief pause to check in and recalibrate can prevent so much rework or regret down the road.

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