Founder Ellen Donnelly helps entrepreneurial professionals build a one-person business around their unique gifts & talent through her coaching business The Ask.
She knows that the people most likely to succeed do not accidentally stumble upon their dreams—they create them. But knowing how to create those dreams can be a challenge. This is where The Ask's range of coaching programs, content, and events come in to help professionals achieve their greatest potential and boldest ambitions.
Although there are often similarities, every business origin story is unique—from starting a nights-and-weekends side hustle that grows slowly but surely, to the diving-in-full-time-with-both-feet startup approach. What is the origin story for The Ask?
ELLEN DONNELLY: Everyone can relate to how challenging it can be to find work that is personally fulfilling.
Since we spend a third of our lives working, when our job makes us unhappy, it’s a really big deal.
In my experience, I was working as an executive recruiter in London and living the dream on paper; going for expensive business lunches, working with top-tier clients and enjoying a well-paid salary. But, under the surface, I was losing confidence in my worth because I knew I had all of these skills and personal characteristics that weren’t being put to use — my creativity, proactivity and problem solving, to name a few.
Any time I’d try and bring them out or use them, I'd feel my efforts shut down by my employers and in time, I became a shell of my former self and dreaded going to the office.
I knew I needed to pivot my career but it took over a year to do so.
I realized that you have to create opportunities for yourself, not wait to be chosen. My new role (that I had hustled hard to get) was like night and day, which confirmed how key it is to be in an environment where your skills and attributes are celebrated. Funnily enough, this environment was extremely entrepreneurial and we were making up a lot of processes from scratch and I thrived. But some years in, I’d outgrown the role and with it being a small team, I couldn’t progress much further.
It dawned on me that I had spent my entire working life helping other people take big leaps and succeed in their entrepreneurial careers, so, instead of waiting for my dream role to appear, I decided to create it for myself. I could provide myself with the security and fulfillment I was looking for.
I invested in a coaching qualification, launched The Ask coaching and, gratefully, have never looked back.
You help ambitious, entrepreneurial professionals decide & plan their next career move or business idea so they can feel clear and excited about their future. How did you go about establishing focus for The Ask? Has this focus changed or refined over time?
ED: After my early career experiences and successfully mastering the process of creating work I love, I have always been clear that helping others do the same would be a priority for my business.
I really enjoy helping clients get clear on their next steps and build businesses around their unique talents — not feel they have to squeeze themselves into others’ definitions of success. This is easier said than done however, and I knew from speaking to so many people how unclear and undecided they were about their professional lives — there is just so much choice these days and not enough strong guidance.
This focus will always form the bedrock of The Ask.
But how I go about supporting my clients (my services) and how I communicate with them (my sales & marketing) has evolved from year to year, based on what I am learning about my niche and my own abilities and interests as a founder and coach.
I am obsessed with the problem of people finding the right work-fit for them, but remain open and flexible when it comes to creating the best solution. I have experimented with 1-1 and group coaching programs, running big virtual startup summits and exploring video courses or workshops for corporates. Each product, pivot or position change leads The Ask ever closer to finding the perfect solution to my dream clients’ biggest career questions.
How do you shape your business into exactly what you want, and not let its scope or services creep out into other areas that aren’t your primary focus (even if there may be opportunity or client requests in those areas)?
I spend a lot of time working ON my business (not just IN it) to ensure that the focus remains on solving the core problem for my customers. Whether that be checking in on my energy levels towards ideas and listening to what I enjoy or don’t enjoy doing in my business. Changing it up when it needs to be. That’s my own mission, after all.
And lots of professional development and courses for myself, too! Life long learning is key when you don’t have a boss to guide you. I’m a big advocate for hiring coaches to support me with strategic decision-making when needed. The right coach has the ability to help me look objectively at the products and offering and optimize them over time.
It’s easy to get stuck in one way of looking at your business, so their role has been to help me to experiment and push the boundaries.
An example of this is that I recently decided to launch and subsequently pause a YouTube and video course offering. This was scope creep in a way — after being told how powerful the channel is.
However I did not enjoy the process as much as I’d hoped and realized three months in that my time was better spent refocusing on areas of the business already generating revenue. After checking in on how I was feeling about it and looking strategically at my financial and time investment, the decision to pause was easy. Making rapid, but well considered decisions is one way I ensure things stay focused. Often startups will practice an 80/20 rule, where 80% of your work and offering remains focused on the core mission and you save 20% for creative projects which is a great way to look at this.
What has been the most significant unexpected thing you’ve learned—about business, life, or yourself—in the process of building The Ask?
ED: The most unexpected lesson has been that business growth and personal growth are one and the same when you are a solopreneur. I understood this conceptually before I began The Ask, but when you are actually in the day-to-day, it becomes incredibly clear that you learn SO much about your own personal development gaps and needs through your business.
In a way, I am in a relationship with my business.
It is a mirror to my behaviors, thoughts, feelings and therefore my actions and is often a reflection of how I am doing in myself. For example, self-belief, confidence, and focus are an essential part of the business building journey and overlooked for hacks.
I am a huge advocate of a clear strategy and direction (those give you focus) but without a positive mindset, not a lot will happen.
To summarize: business building IS personal development.
When you start coaching with new clients, are there any obstacles that usually seem insurmountable to entrepreneurs which are actually quite common and even easy to tackle with the right tools?
ED: There are! The biggest obstacles for those pursuing entrepreneurial paths are actually quite similar across the board. Because of this I’ve come to call them the four horsemen of early stage entrepreneurship! Those are a lack of one or all of the following: time, money, confidence and focus. When it comes to creating something that doesn’t yet exist in the world, the reason so many people stay stuck in motion (and end up working with a coach) can usually be traced to one or a combination of these factors.
I’ve also learnt what methods usually help people to overcome them, too.
I have a free guide to help people diagnose what’s most responsible for holding them back from building their dream business, readers can download it here and then there are suggestions to move through whatever block is most present, too.
If you’re thinking about or are in the early stages of starting your own business or a creative project but are struggling to make real progress, take this quiz and finally diagnose your biggest blockers, and discover the steps you need to take to make that dream business a reality!
I'd love to learn more about what it looks like when you start work with a new client. Can you give me an idea of how on-boarding works—is there a system, or is it totally unique each time? Any must-have tools or critical steps that make it work?
ELLEN DONNELLY: For my 1-1 clients I’ve got the process down to be fairly consistent. That includes them booking an initial discovery call, for up to an hour. This ensures their coaching needs and questions are a fit for what I offer and that there’s chemistry there.
If that’s positive on both sides I would then follow up with the admin parts (boring but essential!) e.g. a coaching agreement, invoice, calendar invitations, forms etc.
The more interesting part is the ‘pre-coaching questions’ I then share.
Many clients take 30-60 min answering these, as they are quite in depth.
It means that by session one I have a pretty good sense of the person to hit the ground running. Then we stay in touch inside their private coaching portal between sessions, too.
There are a range of software and tools that help me with these things, but its pretty manual still as its a high touch service (not self-serve like some product companies would have).
What is a skill you have that you don't consider a typical "résumé skill," but which has contributed to your success in a meaningful way?
ED: That is tricky!
I think it is my ability to ask good questions and be super analytical to get to the heart of an issue. I loved being paid to be curious!
Throughout my life I have always been curious about understanding people; what makes them come alive and what holds them back from making real change or tackling problems. Even my History degree and dissertation I focused on the every day peoples’ lives and what was going on with them at a micro level.
This love has led me to a place of pattern matching and being able to pick up quite quickly on where someone is at, what options they might have, and how they can approach their next steps. This has come from working with or coaching thousands of job seekers and clients over the last 10 years and coupled with a knack for asking the right questions that can elicit the all important ‘aha’ moment. This allows my clients to gain deeper understanding into their unique challenges, interests and aspirations as well as giving them the tools and insights they need to make big changes. Given that coaching is designed to be transformative, the more powerful the line of questioning, the greater the positive impact on the client.
Being able to change people’s lives through asking the right questions has allowed my business to grow through word of mouth referrals for one, and has contributed greatly to my success.
Given that coaching is designed to be transformative, the more powerful the line of questioning, the greater the positive impact on the client.
Did you receive any notable advice (good or bad!) when you were just starting out? If so, what was it? And if not, what advice would you give to your past self, knowing what you know now?
ELLEN DONNELLY: One that stands out would be the biggest investment I made in a coach/mentor figure about six months into running my business. I had clients, but nowhere near as many as I needed to feel financially stable (very normal in your first year of coaching!).
This coach helped me to rebuild my messaging, offers and direction and ability to communicate and I was then able to hit consistent sales months to cover all my London living expenses, and then some. I’m so grateful I invested in support early on, even if the investment was scary to do.
However I will say, that there have been times that someone has not taken the time to understand my initial mission and vision for The Ask and provided blanket advice that doesn’t always apply. It's different building a coaching business with a mission, to one that doesn’t have one, and this is something I am now hyper aware of before I take other people’s opinions on too quickly.
It’s something I talk about with clients — beware of ‘OPPss’! (Other People’s Opinions) as there’s no shortage of them when you’re a solo founder. Most people have good intentions with their advice but it's not always executed perfectly!!
How often do you get new ideas?
coming up with new ideas is a challenge
my brain is always overflowing with new ideas
How hard is it for you to follow through on your ideas and make them happen?
I have to force myself to follow through on things
I love carrying out tasks and completing things
What does your work-life balance look like right now?
I live at work!
I NEVER WORK
I struggle to sit down and get work done.
What’s the #1 thing you recommend outsourcing so that you can focus on the parts of your business that really light you up?
It would be such a personal choice! I’ve tried outsourcing content creation, and financial tracking, and later took both of them back, for example. Sometimes you need to be the voice, or have a handle on things like P&L. So it depends on your sweet spot and strengths. I like outsourcing things which can grow The Ask's online presence such as digital marketing or partnerships.
What’s your favorite non-work thing right now?
I am actually really into Improvisation — aka Improv comedy. I’ve been learning or performing with a group for a few years and also go to a lot of shows. It’s something silly and fun, after being serious at work or whatever, just to wind down. But it’s also a great way to practice traits that can be helpful as a business owner: communication, confidence, adaptability, team work, listening. I didn’t intend for it to help with coaching but it has haha!
CLOSING: Any other thoughts or tips you’d like to share with fellow business owners & entrepreneurs?
I would just say to always spend time in reflecting.
There is not always an immediate ROI to it, but if you can take deliberate time out to work ON your business, reflect on what is and isn’t working, and how you are staying true to your purpose and vision, you’ll stay on track big picture.
For those without co founders or a team, it can get really lonely, and having the support of others around you for business purposes (not just your partner for example) is amazing.
Get some business buddies, coaches, mentors, communities up and running and you’ll really see how much you can learn and grow thanks to their support too. Even just talking out problems to another human can bring clarity, and even more so when they’ve been there before or can help you to reflect on your business properly.
Thank you, Ellen, for generously sharing your insights and perspective!
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