If I am honest, I have a lot of cognitive dissonance when it comes to asking for help. Both for myself and for others. I feel this most keenly when I am interacting with young leaders and new business owners. On one hand, I expect others, and myself, to work to be independent and figure things out on their own. I think this is great for learning and helps us to understand our abilities and strengths. On the other hand, when I see someone continue to struggle time after time on the same issue it is clear it is time for a different approach.
The trick is knowing when to ask for help and when to keep going. Over the years I’ve learned a few ways to explain to others how to figure out when to dig in themselves or when to ask for help.
Here are a few tell-tale signs of when to ask for help:
- Can someone else do it? – If you are running a business or leader of any type, there is a pretty good chance that there are certain things only you can do. If you are working on something that doesn’t fall in that category, especially at the expense of the things only you can do, it is time to pass it off. This benefits you, your team and your business.
- Are you making any progress? – If you feel like you have been working on the problem a lot, but no progress is being made this is a sign that you might need a different perspective. It may be that you ask someone to give you their perspective on the project or problem and that perspective is all you need to get the momentum rolling.
- Are you feeling overwhelmed? – If your mental and/or physical well being are negatively impacted it is time to ask for help. It may still be something you have to do as the owner or leader, but you don’t have to do it all by yourself. Sometimes all we need to get to a better place is a conversation and support.
- Is it in your wheelhouse? – As a business owner or leader you don’t have to know the answer to every question or solve every problem. In fact, it is detrimental to you and your business to think this way. If you are working on something that is outside of your natural strengths it is likely that it will be harder for you than someone else who has that ability. If you don’t have a team that includes someone with a particular skill set, reach out to your network and find someone that does.
- What does your gut tell you? – If you can’t point to anything else, but something just feels off, ask for help. If you know me, you know my view on this. I like data as much as the next person, but our gut is data. It is data based on our experiences. It doesn’t seem like it because it is more data than we can possibly comprehend. The point is listen to your gut and heed the advice.
As you would suspect, the inverse is true if you are not feeling any of these things. If what you are working on is hard and maybe even a bit frustrating, but only you can do it and deep down you enjoy it reflect on your progress and keep on going.
One Small Step
Take some time this week to think about the things you are working on that aren’t going anywhere and you dread thinking about. Can someone else help you? What higher value work could you be doing instead?
If you are looking for some help, but don’t know where to start please reach out. I am happy to have a conversation about it and it won’t cost you anything but your time.

