This blog is the complement of my previous blog and an expansion of the retrospective that I wrote earlier. I ended up breaking up focusing on people that matter from focusing on things that matter because I was finding it hard to write this particular entry. After all, it was deeply personal and left me vulnerable. Reading the book "Dare to Lead" by Brene Brown also reinforced some of the ideas from this entry as well.

Definition of people that matter

It's taken me a long time to figure out who people that matter are even though the answer is shockingly simple. People that matter are the ones that are willing to care about you, invest themselves in you and be vulnerable to you and vise-versa.

I love the show "New Amsterdam," and the epitome of caring comes from the protagonist, Max Goodwin. One of Max's trademark questions is, "How can I help?" It may seem so small, but it's a very striking statement. It's also very different from "Can I do this to help you?" as this question automatically implies the limits on which you are willing to help. Whereas "How can I help?" is an open-ended question that forces you to put yourself out there and to be there in the way that the other person needs you to be.

Investing in someone is about putting a bit of yourself into someone else's interest where the reward isn't about what you get in return but rather in the growth of another person. To truly invest in someone, it requires you first to take the time to know and understand them. It means that you are vulnerable to their needs to empathize genuinely.

I found writing about being vulnerable the hardest to do as it's the one that creates the rawest of emotions. At the heart of it, vulnerability is the pre-requisite to both caring and investing to do it well. Vulnerability by nature is scary, but it is the pre-requisite for relationships that matter. It takes vulnerability to say the words "I care," no matter how scary it may feel. It is scary because there is always the risk that it won't be reciprocated back.

Equal but different

The easiest principles are always the hardest to implement, and this is no different. What makes this particularly hard is the notion of equal but different. Our ability to care, invest and be vulnerable is different based on who you are. One of the most pronounced lessons I learned as a mentee was when one of my mentors pointed out to me that a mentorship relationship goes both ways. As much as it was his responsibility to mentor me, it was equally important that I was mentoring him in return. As a result, it meant that I had also to care, invest and be vulnerable in that relationship.

How it manifests itself between people of different circumstances is different. Figuring this out is often very hard as it takes time and investment from both parties. Figuring out always means trying, failing, adjusting and compromising, but the results can be a wonderful lifelong relationship.

Why it matters to me

Mentorship always has been a massive part of my life and mentorship is often the by-product of focusing on people that matter. You see this manifested in how I've always set up the organizations that I'm responsible for and where I spend my time outside of work. Mentorship means caring, investing and being vulnerable to another person. What exacerbates the situation is I tend to be a person who is either "all-in" or "all-out." So this usually means that focusing on people that don't matter is exceptionally costly and often leads to heartbreak.

Putting people in the right box

When I was younger, I had more energy and emotional capacity. This part of my life allowed me to be more unconstrained about caring about people. As I got older, I had to become more thoughtful about who I was focusing on and how I was going to focus on them. Being a leader in an organization compounds the issue as my organization expects me to be mentoring others.

For the sake of self-preservation, I created natural boxes. For instance, while I have a few different boxes, the most straightforward boxes are a "work" box and a "personal" box. My "work" box is about strictly professional relationships. The "work" box is about working within the constraints of what's best for the employee in the context of the organization. The "personal" box is a much more expensive one where the limitations are what's best for the person as an individual. So I often take some big bets and risks. Frequently the payoffs can be significant. I've seen some people grow tremendously because of it. As an example, when I was at Deloitte, we had traditionally brought in co-ops only from the University of Waterloo, which at the time was the Tier 1 school for technology companies. But someone I cared about had previously dropped out of the University of Waterloo and was going to Ryerson University. Ryerson was considered a much lower-tier school at the time. I took a bet and put my reputation on the line by hiring him. However, by assuming that bet, this individual was able to leverage that experience to become one of the most successful people I know today.

You ideally want to put each other in the same category of boxes. Heartbreak occurs when the boxes don't match. Where I struggle is too often that I am willing to put people in the personal box, but that isn't reciprocated. In this circumstance, the problem isn't on their part - it's on mine in my ability not to recognize the situation, and I did not adjust. The result is often a heartbreak.

At the same time, I am also fortunate. I have a few people in my "personal" box, and I often feel greatly rewarded. Beyond the individual I referred to, I was reminded of this as well in a quick chat conversation on Sunday night with another good friend. I had shared with her that I was feeling very down. She was very defensive for me as she always is. She also shared some tough news about her with me. I also shared my previous blog entry with her. What touched me is that after she read my blog entry and that read the blog entry about my retrospective that was linked. She then volunteered to be my accountability buddy. What I loved about the exchange was this though:

• I'm important to her, and in her way, she always rises to protect me and be there for me
• She allowed herself to be vulnerable to share some tough news with me
• She puts herself out there to be my accountability buddy

How can I not ask her to be an accountability buddy when the only attribute of being that buddy is someone that matters to them? I'm fortunate to have two accountability buddies now.

So What?!?!

It is essential to focus on the people that matter in the right context. Investing in that relationship doesn't come easily as it takes time and requires a significant amount of vulnerability. However, focusing on the people that matter can be extremely expensive. Being in unmatched boxes ends up creating a lot of pain and friction. In my case, it often ends up putting me into an incredible emotional tailspin.