My dad used to tell me, “Be careful what you ask for.” Apparently, he was a lot smarter than I ever gave him credit for. A few weeks ago, I started an interesting journey where I asked some people I trust these three questions: 

  1. What is my greatest strength or skill?
  2. What is my greatest weakness or gap?
  3. Where do I have the greatest opportunity to improve?

The answers I was really the most interested in were the second two, my weaknesses and my opportunities. I was clear when I asked these questions that I wanted to hear the truth – that’s why I used an anonymous survey to ask them. I wanted people to be honest and gave them a permission slip to be a little brutal. When I asked them not to hold back, I knew that the responses I’d get back might be challenging to hear. They were. 

Let me begin by sharing this. Nothing that anyone shared was shocking to me. I feel like I possess a decent level of self-awareness, and with that, I have some basic awareness of where my gaps lie. That said, being aware of where those gaps exist and being intentional to address them are two different things. 

Taking this one step further, when people openly tell us our weaknesses, they’re going out on a limb for us. We’re asking them to get uncomfortable – they’re stepping out and taking a risk to help us be better and go deeper in our lives. That leaves us with a big responsibility. Choosing not to address those weaknesses once people have shared them is wasting a fantastic opportunity.

I knew that the responses I’d get back might be challenging to hear – that ended up being the understatement of the decade. Like dad said, “Be careful what you ask for.” Having people name the areas where I am weak was harder than I thought. My ego started to get in the way, and I had to work hard to keep it in check. Knowing that they could see some of the gaps I thought I had hidden away so well was daunting. 

I had asked, and they had answered. Now, it was all out in the open. It felt kind of like being naked in a crowd – very exposed. With that in mind, and the responses to my questions in hand, it was time to make some changes. So, that’s what I’m doing, and I want to share my journey with you. Here are the weaknesses people shared with me, like lit sticks of dynamite, and what I plan to do about them…

1. Follow-up, response time, and emails

One of the main things I got called out on is the challenge I have in being responsive. When I asked the question about my weaknesses, I knew that this would be at the top of the list. In fact, over 50% of the people who responded to me pointed this out. I’m assuming this came from both clients, coworkers, and friends. Truth be told, I’ve wanted to improve in this area for a long time but have always been too “busy” to set up a good communication strategy. Frankly, being busy is the main reason I NEED to set up a strong communication strategy, so here goes…

My plan to grow in this area started with cleaning out my inbox. The number of emails in there was embarrassing. I responded to all the open items and filed everything else in its appropriate folder. I unsubscribed to all of the email lists I am on that have not proven valuable to me. The process was like cleaning out the closet. When I was done with that, my inbox held nothing. Zero was my new best friend. Before the next round of messages came in, I created a folder called “Action Required.” Now, I check my inbox every day at 8:30, 12:30, and 4:30. Emails get responded to and filed immediately, and things that require a more in-depth response get put into the Action Required folder so that I can circle back to them. I’m letting people know I received their messages, even if my more detailed reply will be held up for a bit. I feel like a new man.

2. Setting clear expectations & overpromising

This ties closely to my challenge with being responsive, and again it probably came from both clients and coworkers. Again, when “busy-ness” is a challenge, it can be tempting to set vague deadlines or slip into over-promising on deadlines to make people happy. This is a strategy that backfires almost every time, and leads to people reaching out to me asking, “When can I expect…?” It’s frustrating for them and does nothing to build up my own reputation. I could try to use that busy-ness as an excuse, but instead…

My plan to grow in this area is actually pretty simple. I am going to set hard deadlines whenever possible, and I am going to work hard to use my tools more diligently to track my progress. I am also going to be intentional in setting realistic expectations with the people in my circle and not overpromising in the moment. Reflecting back, one of my first mentors taught me, “Under-promise, and over-deliver. And, always keep your word.” It was good advice. Being hyper-aware of those moments where I fall into this trap is the key. I’m also working to improve my delegation, which was another weakness people shared with me. This would release me from some of my personal stress and help me to meet those deadlines even more quickly. 

3. Trying to make everyone happy

Weakness number two, overpromising, is hitched to this next weakness – being a people-pleaser. I genuinely like to please the people in my circle. This includes my clients, my family, my friends, and my team. To be completely transparent, I derive some of my own self-worth from making other people happy. Before you remind me that this isn’t healthy, let me say that I already know that and I’m working on it. It is, however, a vice that I struggle with.

My plan to grow in this area is to remind myself that it’s OK just to be OK. My need to perform for other people, and to please them (sometimes at my own expense) isn’t necessary. I’m going to practice saying “no” and allow myself some room to tell people I can’t. I’m also going to work on something I set aside alot, my own self-care, which leads me to weakness number four…

4. My health

When we’re busy and focused on everyone else’s needs, it can be really easy to neglect our own self. Sometimes we look at self-care as if it were selfish, like there’s something noble about discounting our own wants and needs. The reality I am experiencing is that we cannot serve others well if we’re not in good shape ourselves.

My plan to grow in this area hits three main areas. First, I am going to continue strengthening my own physical health by continuing to run with my wife, the kids, and our dog. I’m rekindling my love for skateboarding with my son, and am also working on my diet to make sure I have the fuel to be physically active. That’s not all, though. To help maintain my mental and spiritual health, I am making moves as well. I’ve returned to my morning ritual of meditation, prayer, journaling, and time in scripture. Throughout the day, I’m feeding my mind with books and podcasts. And finally, in the area of my relationships, I recently spent a long weekend away with Cristina, and I’m also making time to digitally and socially connect with family and friends… at a distance.

5. Thinking bigger, being more strategic

This was the last theme that showed up. To be honest, if I had heard this only once, I probably would have taken less notice. Unfortunately or fortunately, it showed up in the responses a few different times in different forms.

My plan to grow in this area begins with analyzing my goals and dreams to see where I should be stretching myself more. It also involves me asking myself this short, powerful question, “Why not me?” This one also impacts the way I think at work. Again, I should be thinking bigger, grander, and wider for my clients – constantly stretching them to reach their full potential as well. That’s what strengthening this weakness really means… making moves and adjusting my mindset to help achieve the full potential that’s out there. 


So there it is… my journey into exploring my weaknesses and my opportunities to grow. This is about as far out into the open as I can drag it. I wanted to share this as transparently as I could to let all of you know that whatever you find on your own list, it’s OK. The things you’re struggling with are normal – you’re not unique. Having weaknesses is not a sign of weakness… it means you’re human. Each of us is a work-in-progress. 

The most dangerous thing any of us can do is to ignore that, or think to ourselves that we’ve got it all figured out. That kind of thinking keeps us from seeing and exploring all our opportunities to grow… and that’s not the kind of life any of us should strive for. 

The second most dangerous thing we can do? To think we can carry all of our weaknesses alone. I need help. So do you. Alone, in this world, is not an option. We need our families, friends, teams, and our faith to travel these paths. We need them more than ever when we start working on our own growth and addressing our weaknesses. This is hard work, not to be done solo.

I want to thank all the people in my circle who were honest and open with me. That took courage. I used the image of the hands presenting a gift in this post because that’s what this was… a great gift from them to me. Unwrapping it came with some challenges, but once the gift was out of the box, it was beautiful. 

To be fair, I found a lot of joy in this process as well. People shared a lot of strengths with me that I am really proud of. They said I am real, authentic, open, and comfortable being vulnerable. They told me I am creative and visionary and have an enthusiastic and positive “can-do” attitude. People called me caring, kind, and a good listener. They acknowledged my writing talent. All of these pieces of positive feedback helped me repair my bruised ego a bit. I liked hearing it. These are the kind of things I’d love to have people share at my funeral… the things we should make sure to tell other people before they reach that point.

The Takeaway

This exercise, having others that I trust anonymously share my strengths and weaknesses, has been powerful and intimidating all at the same time. Once I set my ego aside and looked at people’s insights through the lens of their care and coaching rather than judgment and criticism, everything changed. From there, my mind was open and ready to start exploring the shifts I need to make.

Now, my challenge moving forward is to extend my progress long-term, past these first few weeks. My challenge is to create the rituals and habits that will help me create a lifestyle around these adjustments, not just short-term moves that evaporate like dew on a summer day. 

This leads me to you…

My encouragement to you, as you’re reading this, is to consider asking those same three questions I began with. Specifically, open yourself up to exploring your weaknesses. Ask some people in your circle who you trust to contribute to the process with you. Ask them to help you grow. And remember, that growth sometimes requires a little pruning…

Thanks for being part of my journey! – John Gamades

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