Development, Leadership, Motivation, Planning

5 Questions That Lead Leaders

As a leader you spend a lot of time thinking about others and their professional development. But do you spend enough time thinking about yours? More specifically, do you spend enough time evaluating your current role and its contributions to your future self?

Last week I woke up and I wasn’t particularly interested in Chip and Grey. It was the first time in 3.5 months that I wasn’t interested in feeding the two squirrels, but it wasn’t the first or last time I would question if my current role was fulfilling my professional needs.

It’s easy to forget about your own goals when you’re managing a team with many goals of their own; goals that you will help them achieve. But if/when you wake up one morning and you’re not particularly interested in seeing said team members or you can’t remember the last time you discussed your career goals with someone, I encourage you to set some time aside for some personal and professional interrogation.

Here are 5 questions every leader should ask themselves on a regular basis: 

  1. What were my expectations when I took on this role? (Were they met or can they be met?) 
  2. Am I going to learn any knew skills in the next 12 months? 
  3. How do I feel about the field/industry? (Am I passionate about it?)
  4. Does the culture of the organization align with my values? 
  5. Is there room to move up or laterally within the organization? 

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Why should you ask these questions? Because part of being a great leader is being able to recognize when a role is no longer contributing to your own professional and personal goals. In a previous blog post I discussed how identifying a company’s limitations can change your approach to your team’s training and development, and it’s important to not forget about your own development in the process. The only thing harder than leading is leading without experience.

Take some time to interrogate your current role and ask yourself 5 potentially revealing questions. You may come to the conclusion that you’re happy where you are, or, you may realize that it’s time to take a different route. But one of the most important things you can do as a leader is keep a map in the glove compartment and keep an eye on your personal road. A leader without a map will eventually lead others in the wrong direction. 

– Brianna

Leadership, Loneliness, Planning, Self-Care

One question you should ask yourself before taking on a leadership role

Prior to taking on a managerial and/or leadership role, I highly recommend asking yourself one question: How well do I handle loneliness? 

Your answer should not decide whether or not you accept the position – there are plenty of other, more important things to consider. Your answer should, however, decide what support systems you will need if you choose to take on the role. If you’re reading this and are already in a leadership role, join us and ask the question.

Loneliness is frequent in leadership. It’s not constant and it doesn’t mean you will literally be in a room by yourself more times than not. But loneliness can exist while sitting in a boardroom full of people. Loneliness can exist during your birthday party. Loneliness can, and certainly will, make an appearance on your commute to work. Loneliness is a force, a tool of isolation, and above all, an underestimated symptom of leadership.

You’re no longer the one who gets to sit with your co-workers and trash the boss’ decisions. You’re the one who now makes, intercepts, over-rides, rationalizes, and presents the decisions, including the difficult ones. Very few people will understand what it’s like to make 452 decisions (big and small) on your own, in your own head and in a short period of time. This is how you miss birthday parties while you’re cutting the cake. This is how you miss your bus stop because you’re weighing the pros and cons. This is how your mind and body wind up in two places at once. Some decisions you can debate with a co-worker, friend, or family member, but for the most part, you’re on your own. Some decisions will take seconds, others minutes, hours, or weeks. Which is why, as a leader, it’s critical to be aware of and interrogate your ability to combat loneliness.

I recently stumbled across a motivational talk by Gary Vaynerchuck, entrepreneur, author, speaker and internet personality. Over a period of 5 minutes, Gary had me nodding hard in agreement, applauding his transparency, disagreeing with more than one statement, breaking out in laughter, and irrationally thinking, “Thanks, Gary. But we’re not all ’emotionally stable-as-&#@!’ like you are!”… It’s a great 5 minutes! Gary carries us through the emotional roller coaster of leadership, and I encourage you to sit back, relax, and enjoy the talk…

*Warning: Language used in this video may be offensive to some viewers*

The Untold Truth About Leadership – Gary Vaynerchuk | Motivational Talk

…Let’s revisit one of Gary’s thoughts:

“I know that I am emotionally stable-as-&#@! and it’s intense for me. I can’t imagine people that are not as fortunate as I am…” (3:55-4:06)

Gary recognizes that being in a leadership role AND being emotionally stable is a luxury – a rare luxury – and recognizing this will have a large impact on your career as a leader. It will define your approach to self-care, it will determine how quickly you can make decisions, and it will influence your ability to manage how lonely it can get “at the tippy-top.” I admire Gary’s emotional stability (even though my initial response would have you think otherwise), but my jealousy-ridden response simply reminded me of the fact that, like many others, I am a leader who will always have to work hard to combat loneliness. Plain and simple. I am also a leader who, in the past, made the mistake of waiting until I noticed signs of burnout and isolation (by choice) before asking myself, “how well do I handle loneliness?” Which is why I am encouraging you as a leader to ask the question sooner rather than later. And if necessary, more than once.

As leaders and managers we are consistently asked to be pro-active in the workplace. We are required to forecast the results of our decisions based on the known and the unknown. We prepare for failure but aim for success. We have (or should have) a contingency plan if someone is sick or walks away from a job. But do we prepare for our own loneliness?

Prior to taking on any managerial and/or leadership position, ask yourself one question: How well do I handle loneliness? 

If your answer is anything but “I’m emotionally stable-as-&#@!,” create a support network. Create a list of people and organizations you can call at any time. Write down your interests, hobbies, and passions and post them somewhere where you can see them. Remind yourself that it’s OK to take time off, or, feed a squirrel and take a break from humans altogether. Chip is a surprisingly good listener.

Be pro-active and try to prepare for your own loneliness in the field of leadership. The job is yours and only yours, but don’t allow it to have your birthday cake and eat it too.


Employee Relations, Leadership, Motivation

Be the fuel, not the fire

Two months ago on a particularly slow afternoon, I noticed a squirrel sitting in the tree outside of my kitchen window.  It had a chip in its left ear. Black fur, patches of brown here and there. I scrambled to find some trail-mix before it moved on to another tree. I slid the window open, quietly, trying not to startle it, and dumped sunflower seeds, peanuts and dried cranberries onto the window ledge. An hour later I returned to the window and the trail-mix was gone. I was thrilled and couldn’t wait to tell my partner about my new friend when he got home.


“WHAT!? YOU FED A SQUIRREL?”… “What if it comes into the apartment!?”… “IT’S GOING TO BE LOOKING FOR FOOD HERE NOW”…”BAAAABE!”… Well, it wasn’t quite the response I was expecting, but I quickly began to list all of the great contributions the squirrel could make to our daily routine.

In my first year as a manager I was told to always defend my employees. If a customer issued a complaint or an employee made a mistake, it was my job to defend them. But I quickly began to re-think what it meant to defend someone. “Defend” is a tricky word and can easily be misunderstood. Being on the defence doesn’t necessarily produce a solution, nor is it a great way to de-escalate or progress a situation in a productive manor. The last thing you want is to hit a wall or even worse, become one yourself.

So let’s change a word and see what happens…

Always support your employees. The best way to support your employees is to create perspective. Whether it’s for yourself or the customer on the phone, take a moment to look at the bigger picture. People will make mistakes (including you and me), but as a leader it is not only your responsibility to hold your employees accountable, but to inspire them to make improvements and take on future projects with confidence. Here is one simple thing you can do to immediately create perspective in a challenging situation:

  • List 3 reasons why that employee is a great contributor to your team

Recite them in your head, write them down on a piece of paper, or say them out loud. As a customer is giving you an ear-full or you see someone press the wrong button, remind yourself of what makes that person a great employee. Trust me, sometimes this will be easier said than done, but dig deep and start listing.

Having that employee’s contributions fresh in your mind will change your approach to communication and inevitably, your approach to management. You will address the contributions first, then the feedback, then next steps.

Perspective is the difference between coming in HOT; “Bob, I just had a customer scream at me for 25 minutes! There are no product pictures on the website. Fix it!” And coming in cool and collected; “Bob, thank you again for all of the hard work you’ve put in to the company’s website. I just received a phone call from one of our customers and they’ve noted our product photos are missing from the website. Can you look into it right away? Thanks!”…Which Bob do you think really wants to fix that website?

So before you hang up that phone or walk in to your employee’s work space, make that list, create perspective and take the heat down a notch. Feed the squirrel some peanuts and be the fuel, not the fire.

– Brianna

Featured Images: ©Brianna MacLellan