We’re excited to introduce you to the always interesting and insightful Kieran Dotti. We hope you’ll enjoy our conversation with Kieran below.
Kieran , thanks for taking the time to share your stories with us today – Do you take vacations? Why or why not?
I do take vacations. There were many years while I was employed that I did not. When I was starting out, I was working perma-lance jobs where I did not get any vacation time, and I couldn’t really afford to go anywhere either on a starting salary. Then, when I’d finally found a job where I earned PTO, I was so busy, the company so understaffed I felt like I couldn’t ever step away without causing myself more stress. If I did take off, I would still wind up fairly connected to my team. So, when I went into business for myself, I vowed to set better boundaries and expectations, and take the time off. I wanted to create a life that allowed me to travel and rest without guilt. I build holidays and vacations into my contracts and give my clients plenty of time plan accordingly. As their business manager though, most of the preparation does reside with me and I ensure that top priorities are addressed prior to my leave. I may check the email a few times, but I have to say that so far, I have done well in choosing who I work with and have found people who are respectful of the time away.
The best advice I can give is to TAKE THE TIME OFF! Don’t learn the hard way like I did and get completely burned out and only then make changes. If you’re a solopreneur or have a very small team, and you truly feel you can’t step away, then you have some work to do within your business operations and delegation, so speaking with a Certified Online Business Manager®, like me, is probably a good first step into gaining some breathing room for you!

Kieran , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I am a Certified Online Business Manager ®. I step in as the CEO’s 2nd for small, growing businesses, and help to manage teams, ensure that there are proper systems in place, and continually optimize the business for peak efficiency and profitability. I’ll help hire and train new team members, implement project management systems, manage launches, help business owners set up online stores or coaching programs.
All those things work together to create more time and breathing room for business owners. Room for them to create and work in their zone of genius. So often when we start our businesses it’s just us figuring out everything from bookkeeping to marketing to sales, even though none of those things are what the business does like in the case with coaches, authors, cooks, doctors, therapists, spiritual practitioners, etc. and the entrepreneur life asks us to be decent at far more than what we’re trained for in order for the business to succeed. But the truth is, you can only get so far alone. Sooner or later, you must bring in specialized help. Which is where I come in! And while I’m not an expert at all things, I know how to manage, and when it’s time to bring in additional support.
One of the things I’ve been most proud of is hearing my clients discuss in their coaching programs, how nice it is to have someone to rely on. For them to be able to tell people, “Kieran’s great. And whenever we want to ___ next month, I know that she’ll help us get there”. And in saying so, use that information to inspire their clients to delegate, grow and think big. That they can be a successful example for their clients, in part because of what I do for them, just makes me light up. I help a wider range of people by helping a select few, and I absolutely love that ripple effect!

We’d love to hear the story of how you turned a side-hustle into a something much bigger.
At the end of 2020 I left a company I’d been with for almost 7 years, totally burned out. I had nothing lined up, but I just had nothing left to give as its COO. After about a month, a company who I’d previously partnered with reached out for some help with their M & A goals. They needed someone who understood the entertainment distribution business and could manage the integration steps as they bought companies. Since I had nothing else lined up, I figured, why not? It would have been great as a side-hustle, but it was the only hustle for a while.
It was at the end of 2021 when I met a Certified Online Business Manager ® through a networking site called LunchClub. By this point I had a nice long list of all the must-haves and would-like-to haves from a new job. So, when she told me about what she was doing I was super intrigued. Here was yet another thing I didn’t know was an actual job and YET, I was sort of already doing it as a consultant. She pointed me where to get certified and the rest, as they say, is history! Within 6 months, I’d established the business officially, and found some more clients to round out my days. For now, I’m quite content as a solopreneur, having doubled my business from year 1 to year 2, finally breathing easily financially, and knowing that this can really work for me as a career. I truly can’t wait to see what else is in store.
Moral of the story, network, network, network. You know never know where the conversations will point you!

How do you keep your team’s morale high?
I know for me when I first started to delegate and manage, I was working for smaller companies without HR and without any leadership training. I know I didn’t always get it right. But as is the case for all things in life, in my opinion, you just must learn and grow from your mistakes. Be accountable and apologize sincerely when you do get it wrong. There’s a saying I’ve seen on LinkedIn a lot, that people don’t leave companies, they leave bad management. Similarly, people will also stay at a company that isn’t great, just because they love who they work with, and they know how hard that is to come by. I’ve certainly done it.
On a practical level, managing a team has a few basics – always have 1:1 check-ins at least monthly, have a project management system where all things are tracked, and to lead with kindness and understanding. But it is so much more than this!
I’ve recently been reading “All In: How Great Leaders Build Unstoppable Teams” by Mike Michalowicz. The quick synopsis: the key to having a great team, is to have people who are just as invested in the company’s success as the owner is, they’re “All In” and stay with the company for many years. And that doesn’t necessarily mean they’re all actual monetary investors, it just means they care deeply. He outlines a series of steps, starting with hiring, to achieve this. The chapter I resonated with as a former employee and now business owner, talks of empowering the team by fostering psychological ownership – by outlining the goals for the year or quarter and relying on the team or person’s suggestions of how to get there. In many places I’ve worked at I’ve had zero idea if it was a good or bad year, what the company’s goals were, or why I was being asked to do X when I clearly saw in my day to day that it was a bad idea and that Y would have been so much better. Your employees are the ones in the trenches and if you don’t trust them, why should they trust you?
Which brings me to my 2nd biggest takeaway, which shouldn’t be a surprise, but companies really do struggle with it – Maintaining a secure and accepting environment. If people don’t feel that they can speak freely for fear of firing or retaliation or at the very least, that they’re just never listened to, then they’ll do the minimum and move on to where they feel safe and appreciated. Simply put, if you take care of your people, listen, and invest in their success (to the point where you’d recommend them to another company because you know they’d be great) then they will happily come in, do their best, and want to stay for years to come.

Contact Info:
- Website: https://www.onthedottmgmt.com/
- Instagram: onthedottmgmt
- Facebook: https://www.facebook.com/OnTheDottMgmt/
- Linkedin: https://www.linkedin.com/in/kierandotti/
Image Credits
Eric Boguslavsky for all but the grand canyon and waterfall pictures

