How to use a project management software. If you’re delegating something that will take some time to complete, one of the easiest ways to see how the project is progressing without finding yourself pulled into a micro-management role or back into the actual work is to use project management software. There are a ton of options, so find the one that works for you. We use Asana and when we’re putting together a new event, I will typically go in and create the appropriate Asana board (usually copying and pasting a checklist of To Do into the board and removing items that aren’t applicable for this event). Then we have a team meeting where I assign each task out along with a deadline. The software will email the team consistently to remind them when it’s due. They put their notes inside the software for easy reference, and it makes it simple for me to see if a project is moving along or not.
As part of my series about the “How To Delegate Effectively and Be Completely Satisfied With the Results”, I had the pleasure of interviewing Stephanie Scheller, founder of Grow Disrupt, a San Antonio-based training organization for small businesses.
Stephanie is an accomplished speaker and has been behind the scenes with more than 2500 companies in the past five years to analyze & address their sales, marketing & systems!
She is a TEDx speaker, a Forbes 30 under 30 nominee, a 2020 Woman Business Owner of the Year Award Recipient, a two-time best-selling author, an entrepreneur, a coach and a trainer and dedicated to teaching the same skills that allowed her to build her business from scratch and walk away from her corporate job in less than five months.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Absolutely! So my parents raised us on the Rich Dad Poor Dad books and I always wanted to be an entrepreneur, but ended up taking a corporate job when my original plan A (owning a barn) didn’t work out. I worked there for three years before starting my own business in May 2014. By the end of August, I’d made more money part time than full time and turned in my two weeks’ notice to walk away & run the business full time.
About 18 months in to building the largest and most active sales training practice in Central Texas, I realized I didn’t want to be a sales trainer and had the joy of going through a transition period where I was still running the business and doing well, but trying to figure out “What I wanted to be when I grew up.” I realized that I wanted to help small business owners, but in a bigger way than I had the knowledge for after just a couple of years of being in business, so I started designing events to bring in experts. I would choose the speakers based on their background, then use my knowledge of psychology and how the entrepreneur’s brain works to help them lay out complex concepts to make them accessible and easy to implement for business owners and sell tickets to those events and that’s what I do now! Empower small business owners with the tools and knowledge they need to thrive personally & professionally!
Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?
Oh man! Yes! I remember that first December I had my first breakdown. I’d just finished a meeting with a lady who had said she wanted to hire me, but instead turned it into a big sales pitch that I let run on way too long and by the time I left, traffic had picked up and I was frustrated because it was going to take me twice as long to get home and I had hours of work ahead of me before I could go to bed. I was so overworked, so exhausted and so frustrated that I ended up crying so hard that I couldn’t see straight and had to pull over on the side of the road.
I ended up having the sense of mind to get off the road completely and ended up at Barnes and Nobles, absentmindedly browsing the self-help section. I saw this book by Seth Godin called The Dip: When to Quit & When to Stick and I remember thinking that I didn’t even know if I should keep going or quit or if it was going to be worth it “in the end.” I was at this point where I was making great money, but I was so overworked and had this idea in my head that I couldn’t hire any help until I hit this major financial milestone, so I was doing EVERYTHING from sales to marketing to training to finances, everything!
And I ended up buying the book, going home and finally getting a good night sleep and not even reading the book for months! When I finally did pick it up, I had this moment that I really wished I’d picked it up back then because it created awareness for me about the massive pressure I was putting myself under, but also the goals I was going after and how to weigh whether those goals were worth the strain I was putting myself under. Once I got clear on that, I had the realization that some levels of stress aren’t worth it! And when you have that clarity and set the boundary that some things aren’t worth the stress, you actually create the room for greater growth, while being happier!
And hiring people and delegating is WELL worth it for the amount of stress it takes off your plate when it’s done right!
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?
I don’t know that I look at our mistakes as “funny” per se….I have fun, but I don’t know that I’m super “funny”, even in retelling those mistakes!
I know I made a LOT of mistakes in sales early on. I took deals I shouldn’t have with clients that I knew were going to be a pain to work with (You can almost always tell with those clients! It’s this gut feeling that says “This person is NOT going to be fun to work with, you’re never going to make them happy…stay away!” and I found myself working WAY too many hours for WAY to little money, which really prohibited me from working on bringing on more and better clients so I could scale.
I also was super short-sighted in sales frequently! When someone didn’t want to buy today, I would get salty on them and I burned a lot of bridges. I shake my head looking back on that Stephanie sometimes!
Basically, I learned that whether the sale comes in today, or tomorrow, I’ll be super grateful for it, and everyone has their reasons for why they do what they do, it’s not up to me to sort all that out. It’s up to me to do enough sales activity to keep the business flowing!
And also, when I’m talking to someone who seems like a lot of work to close and is giving me any of my red flags, RUN away!!!
What do you think makes your company stand out? Can you share a story?
I am obsessed with psychology. I am constantly looking for what small changes we can make that will increase our effectivity. There are a million people out there hawking support for small business owners. But if everyone lived up to their promises, we’d have a lot more successful small business owners! Part of the issue is that everything a small business owner learns has to infiltrate their brain far enough and simply enough to be implemented and integrated into the business and not every support agent understands that. For years, I’ve been obsessed with psychology and how to make what we do easier for the small business owners to understand and integrate and allow them to operate at their peak. .
My sandbox is our events! There are a ton of events for small business owners out there. But at our events, I am constantly analyzing and adjusting how the event is set up to maximize each attendee’s ability to absorb the content. Every time we do an event, we find a few more things we can do that no one will overtly notice, but that make the whole experience easier on their brain to process, which means that they are able to be more alert, internalize the content they are learning, and it’s a breeze to implement when they get back to their office!
Now that we’ve been doing events as our primary focus for six years, we’ve built a huge toolbelt of things to do that make our events really stand out. A few examples:
- Our pricing structure: we price at 3000 dollars or 8500 dollars for an event….not 2997 dollars or 8497 dollars because their brain doesn’t have to work to process “3000 dollars” and they can focus more on the other aspects of the event to consider. Additionally, our clients aren’t looking for discounts. They are looking for quality and are smart enough to recognize the games people play with 8497 dollars and are actually turned off by it.
- We only hire professional speakers, who are also active in whatever role they are going to teach about. If they are teaching us how to get PR for our business, they are actively getting PR currently so they know what is working, and how to break it down to make it easy to do the same.
- Our agendas are always designed so the energy flows throughout the day so no one hits hype-overload or cortisol fatigue and can’t process mentally. We plan longer breaks than most events and organize, what appears to be, small touches that allow our audience to connect more intimately with other attendees. That allows them to give the side of their brain that is internalizing information a break from information overload and recovery to prepare for the next speaker.
- We also set up extremely intentional seating at our events to facilitate more conversation — at the Grow Retreat, we use round tables of 6 instead of rounds of 10 so no one has their back to the stage and everyone has the ability to spread out a bit.
- We put the snacks and drinks on the tables so people don’t have to get up and go through a big long line to get a drink at break.
The list continues!
Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?
It’s critical that, as an entrepreneur, you take time for yourself and you show yourself how much you appreciate all the work you’re putting in. That may sound strange, but I’ve learned that entrepreneurs are fantastic at really pushing ourselves and ascribe to the “Living today like no one else will so you can live tomorrow like no one else can.” So we cut our paychecks to be able to afford our team, we work longer hours, etc. And the problem is that we end up with an identity of this entrepreneur who half kills him/herself and doesn’t value him/herself so even when we’ve made it, we can’t see it!
It sounds overly simplistic, but start prioritizing paying yourself AND giving yourself profit distributions — or start working on fixing your margins and costs so you CAN. And give yourself permission to take time off, to NOT work tonight…to leave work early or to take the weekend off!
Your head will go CRAZY when you try this if you’re anything like I’ve been! There’s SO much to get done, and if you leave your team working, you may feel guilty about taking time off when they are working like crazy. Do it anyhow!
Remember that the key to self-care is that it’s at least a little bit selfish! But unless you take time to take care of yourself, you can’t take care of anyone else. So especially when you’re feeling like there’s no freaking way you can take time away, that’s your biggest cue that you’re probably pushing yourself too hard.
Take some time and go do that thing you really want to do.
Celebrate the small wins.
You’re an amazing person. Give yourself permission to recognize that.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?
There have been a couple of people who really impacted me, my now husband, at the time boyfriend, and my Mom. Over the six years I’ve been in business for myself, Matt (husband) has been unbelievably supportive. He’s believed in me and reminded me to be kind to myself, and that I can do this.
My Mom is the reason I got started on this road!
Back in 2013, the company I was working for was falling apart at the seams. They’d had a few people come in to work for them that really took advantage of them, and (on top of being an industry that is really struggling: newspaper) they were really hard up for cash. At the time, I was the head of the retention department for digital sales and when they’d courted me to take over the department the previous year, the only way I’d agreed to do it was if they designed a commission structure for the department since I didn’t want to leave my sales commission to take over a department with 8% retention and try to turn it around for a relatively small base salary. Towards the end of 2013, they started really hurting for cash and made the decision that the commissions for the retention team had to be cut. I spent the next 7 months fighting tooth and nail for my department, and my own commission and they kept promising a new commission structure to roll out, then finding an excuse to not pay on it.
I remember one day in particular, I’d come out to meet with an upset client and try to retain his business for the company and while I was sitting in his office, I got a text from my boss letting me know that there wouldn’t be a commission for this month either. Fortunately, the client had to step away to deal with an emergency in his office so I excused myself, went out to the parking lot and just fell apart. I ended up calling my Mom in tears, at my wits end and with no idea of what to do next.
What I love about my Mom is that she could have sat there and commiserated with me and called the company all kinds of names and told me I was better than that, etc.
Instead, she purchased a second plane ticket for me to fly to California with her the next month before we got off the phone so I could attend an event with her on how to start a sales training business.
That was the start of a whirlwind! As mentioned before, I started my business in May 2014 and by the end of August I had made more money part time than full time and walked away to run my sales training practice full time. But that moment taught me that sitting around being miserably and complaining doesn’t help, doesn’t do anything! If you are unhappy, it’s up to you to take the reins & change what is hurting you.
Ok thank you for all that. Now let’s shift to the main focus of this interview. Delegating effectively is a challenge for many leaders. Let’s put first things first. Can you help articulate to our readers a few reasons why delegating is such an important skill for a leader or a business owner to develop?
Absolutely! To start, I want to admit that I’m a recovering do-it-yourself-er. It took me years to really trust my team with anything important to the business. I operated with a skeleton team and gave them only minimal tasks, usually something that was redundant or supportive to what I was working on. I was fully trained and capable of taking over any task in the company at the drop of a hat and could usually do every part of it better than anyone else. I didn’t realize it, but hiring people who were less competent then me was my way of staying in control of the business and avoiding dealing with the identity crisis I ended up having to work my way through eventually.
It wasn’t until I worked through some of the mindset, communication and identity crisis issues I was dealing with that I started actually trusting my team. Until I did that, we were experiencing growth, but not at the spectacular level I wanted.
When I finally started trusting my team and building up a real team, assigning work (and empowering them to make decisions on their own, I had two major breakthroughs:
- Life was a LOT better! I wasn’t so stressed, I wasn’t freaking out over a million details and less stuff was slipping through the cracks
- We were able to make that exponential growth happen because I was freed up to focus on my energy genius (the things I am GREAT at, like sales & marketing) while letting my team truly own and run the parts of the business they were in charge of.
Our events took a MASSIVE leap forward in quality. Our revenue doubled. Our profit doubled and cashflow and recurring billing stabilized. It was really remarkable that I was so much happier (which came first!) and then the business stabilized so quickly in response to learning to delegate & trust!
Can you help articulate a few of the reasons why delegating is such a challenge for so many people?
I think a lot of leaders struggle with an identity crisis. On the one hand, we have new work to do now that we’ve moved into the leadership phase that is pulling on our attention. On the other hand, a lot of the identity we’ve built over the past period of time revolves around being great at the role we just left! And as humans, we really like feeling competent and capable and dislike the inherent slow learning period of becoming capable at a new task or set of tasks. So when I work with small business owners, I often find themselves blaming their team for being impossible or unskilled when the owner is stepping back in and taking things over, or unconsciously providing conflicting information or not enough information so they can step in and be the hero while still doing the job they are best at. This often leads to a business owner who will “delegate” a simple step in an overall project, but refuses to delegate actual decision making power. So they are creating a self-fulfilling prophecy that no one can do this as well as they can because their team is constantly having to come to them for decisions throughout the process, because the business owner is constantly undermining the decisions the employees make in order to retain their identity as the hero in that arena. It’s complex and layered!
The other issue that I think comes into play to make delegation so challenging revolves around communication. When we are having a team member take over a task that we are competent at, especially if it’s a task that we have been doing for a long time and are extremely competent at, it’s easy for us to skip a step while trying to tell them what to do.
For example, most of us have peeled carrots or potatoes or some variety of vegetable in our life. If you needed to tell someone else to do it who had never done that before, the instructions would probably align with “Grab the peeler and peel the potatoes!” Accompanied by a quick point to the peeler and the potatoes. In that sentence, there’s minimal instructions about what the peeler looks like, how to hold it best, how to hold on to the potatoes so they don’t pop out of your hands, oh and the warning that peeled potatoes are slippery! In the best case scenario, we grab the peeler and quickly peel half a potato and then hand it back to them.
So of course the individual who is taking over peeling the potatoes is substantially slower at it than we are and may peel five potatoes in the time it takes us to peel ten.
In a fast-paced work environment, this can be frustrating to the leader who planned for you to spend 10 minutes peeling, but it’s taking 20 and messing with their timeline.
Now, that’s a pretty simple example. But the same concept can be applied to pretty much anything: making calls, designing graphics, running a sales call, taking care of a customer, etc. There are a million things that we’ve learned to do inherently that make the task easier, but even when we communicate all that to the team member, the team member is often able to only retain a few of those tips at once! We’ve been “peeling the potato” so long that it’s second nature and we don’t even recognize how much skill goes into doing it well and quickly.
So then we get frustrated and tend to just take it over and do it ourselves.
In your opinion, what pivots need to be made, either in perspective or in work habits, to help alleviate some of the challenges you mentioned?
I highly recommend that the business owner who is struggling with delegation take some time to evaluate WHY they are struggling.
We all have a hundred excuses for why we are having trouble. But excuses are exceptionally misleading! They are usually how our brain handles dealing with something we don’t want to face. Maybe we’re a crappy manager & trainer and it’s easier to deal with the perspective that the team is incompetent. Maybe we’ve let employees get away with sup-bar performance for years and now need to call them on the carpet but are afraid it will ruin the friendship we’ve cultivated or turn ugly. Maybe we’re dealing with an identity crisis and we don’t recognize that our role is shifting and it’s scary because we’re used to having to be the fearless leader who is never scared.
When you’re struggling with delegation, I recommend starting with “The 5 Whys exercise”.
The 5 Whys Exercise: Whatever your challenge is, list it out, then your job is to ask yourself why that is happening five times. So if you feel like your team is incompetent. Ask yourself “Why?” and whatever answer you get, ask yourself why again until you’ve asked Why five times. You may find that you didn’t hire the right person. Or perhaps you hired the right person, but you didn’t support them very well.
A lot of times, it will take some work and some introspection to uncover the heart of the issue, but then you can start to address it!
I also highly encourage business owners to realize that when you delegate, part of your job description becomes managing the team! You need to delegate MORE off your plate than you think you do because you need to free up some time to manage and support your team properly. Too often I see a business owner who delegates and then doesn’t check back in until a month later when numbers aren’t being hit or something is being done wrong. By then, the employee has learned how to do it wrong and it’s become a habit. Or it’s been forgotten by the employee because they weren’t used to doing it and it slipped from their mind.
When you delegate, ask questions to ensure they understand, then check-in at predetermined times (This is the key! Let them know you’ll check in “On Monday” but to reach out if they have questions in the meantime and how far you expect them to get by Monday) to ensure that they are comfortable owning the task. When they try and push it back on you by asking you to make decisions pertaining to their task, ask them what they think they should do.
When you check in, ask specific questions about specific portions of the delegated task that you know they might have trouble with to solicit detailed answers rather than a generic “It’s going well!” which is usually code for “I have no idea what I’m doing…but I’m figuring it out rather than admit that I don’t know what questions to ask!”
It’s more work to delegate at first because it’s easier for the employee to put it back on you, or take it over & do it yourself than to ask questions to get your employee to own the task & the outcome, but when you start to train that portion of your brain, you empower you and your team to thrive!
Can you please share your “Five Things You Need To Know To Delegate Effectively and Be Completely Satisfied With the Results?” Please share a story or an example for each.
- How to communicate effectively in any individuals “language”
I am a huge proponent of the DISC communication method. It takes a while to fully integrate it, but it is an extremely accurate tool to understanding how people communicate and how they want to be communicated with. For example, I have one of my team members who is a very high C. I am a high D and I, but a pretty low C. When I first started delegating work to her, I would provide her with my classic short & sweet instructions and expect her to fill in the blanks & take charge of the project. We realized very quickly that she needed more detail from me during the assignment process, and I had to give her space to ask questions so she was fully comfortable understanding what was needed. High D’s aren’t great with questions all the time, so we found a great middle ground and she’s allowed to ask 5 questions, then has to take some action, then can come back with more questions, but 5 is usually all she needs before she can start working and she’s fantastic at finishing the project with extreme detail-driven attention.
2. How we are driven & motivate
While DISC is great for understanding your communication style, and the style of your team so you can adjust to meet in the middle as needed so everyone has the information they need to proceed, figuring out what drives someone allows me to do two things:
Assign projects that someone will be excited about working on
Assign a project in a way that appeals to what motivates them
Both of these allow me to have a team that is super excited & driven to complete their tasks in record time and with exceptional quality.
For example, one of my team members is driven very highly by the collection of information. Whenever I can give her an assignment that gives her leeway to do research, she gets super excited. She loves digging into how things work, and why, and what’s working and what isn’t, and figuring out why. She’ll do research on all kinds of ancillary points to see if there is anything extra that we need to evaluate when making a decision and then bring it to me in a nice, neat, concise package to review with suggestions at the bottom (because she knows that’s important to my communication style) and has a blast with those projects. So every time I have a research project that is going to impact the direction of the future of the company, she’s the one I turn to.
3. How to recognize your own identity crisis & step away
This one is really hard to do on your own. I mentioned the 5 Whys Exercise earlier, but it’s really critical that the business owner is able to step back and even have that recognition. A few critical points that might indicate you’re dealing with an identity crisis:
- You can never get out out
If there is a role that you swear you don’t want to be involved in (such as client work or directing the company), and you’ve trained your employees to handle it but you find yourself constantly being pulled back into or involved in, there are two options: either you might need to train your employees better, or it’s a sign of Identity Crisis. In many cases, it is a sign of Identity Crisis.
- Your team is never good enough
This sign works hand-in-hand with the first one. If your team never seems competent enough to handle what you’ve given them (even though you’ve invested a ton of time in training them), it’s a likely sign of an Identity Crisis.
- You’re listless
Feeling like you’ve lost purpose and don’t know what to do next can be a sign of several different things (such as a loss of vision or being burnt out, which is a dangerous thing. If you think you’re burnt out, check out my article on how to fix that.), but if you’re feeling this in concert with any of the other signs on this list there’s a good chance it’s part of an Identity Crisis.
- You know what to do next, but…
If you know where to move your business next, but constantly feel pulled back to your old job it’s a good sign you’re dealing with an Identity Crisis. I’ve dealt with this symptom personally, and it often comes to me as a voice that guilt trips you into checking back in on your old job (day-to-day projects) to see how things are going (many times, on your day off). Don’t do it! I can tell you from experience, the job that is being done will never feel good enough and checking in too deeply will push you into the spiral that Driven Crazy is dealing with.
If you find yourself dealing with an identity crisis, I recommend bringing someone in that you trust to call you on the carpet when you fall into the trap of having to do it yourself, who can help you walk through the rule of 5 Whys. We definitely CAN do it ourselves, but it’s hard to be rational and logical and recognize the need when we’re in the midst of the crisis!
4. How to set up check-points & proper check-ins with your team to avoid micromanaging
I don’t know why but small business owners have the hardest time with setting up recurring one-on-ones with their team members. Every company I work with, I have to fight to get them to start doing one-on-ones because they feel like they talk to and see their team members daily and it’s a waste of time (after-all, most of us left a corporate job that had a lot of time-wasting-meetings). But once we implement them, the employees are insanely grateful for the feedback as they progress along a project instead of a bunch of feedback at the “end of the project.” And the business owners even admit (usually grudgingly) that it really helps improve the quality of the employees work!
Whenever I’m delegating, I will make sure to clarify when the project is due (and ask if that is enough time), how often we will check in, what check-points I want to be alerted about once they reach them and where I want to be roped in, etc.
When I receive a project update or a first draft, I’m highly focused on highlighting what went well first. Analyzing what I want them to change to determine if this is just Stephanie wanting it “my way” (this isn’t Burger King!) or if it’s truly important to the final quality of the project and then providing feedback in bite-sized increments as much as possible. If there are a LOT of changes, I try and back it out to provide and overview of what needs to be addressed first. I can always get granular later, but if there are structural issues with the SOP my employee is building, getting on them about grammar is just nitpicking this early in the game!
5. How to use a project management software
If you’re delegating something that will take some time to complete, one of the easiest ways to see how the project is progressing without finding yourself pulled into a micro-management role or back into the actual work is to use project management software. There are a ton of options, so find the one that works for you. We use Asana and when we’re putting together a new event, I will typically go in and create the appropriate Asana board (usually copying and pasting a checklist of To Do into the board and removing items that aren’t applicable for this event). Then we have a team meeting where I assign each task out along with a deadline. The software will email the team consistently to remind them when it’s due. They put their notes inside the software for easy reference, and it makes it simple for me to see if a project is moving along or not.
A word of warning! This did take work to train my team to actually use the software. Every time I asked for an update, I asked them to go into the software to put the update in there and I would check in “by the end of the week” to see what they noted. I also had to use the software consistently and put my own notes in so they could see the power of it. But once we all were trained on it, it makes delegation a breeze! Now I can add something & assign it out with a deadline and know it will be taken care of without having to have a meeting to discuss.
One of the obstacles to proper delegating is the oft quoted cliche “If you want something done right do it yourself.” Is this saying true? Is it false? Is there a way to reconcile it with the importance of delegating?
I think this is a cliche that was started by someone dealing with an identity crisis who didn’t understand the importance of training a team and how much further it would get you, and how much happier you are, when you have a team and you can focus on doing the things you’re best at in your new role!
When we’re dealing with an identity crisis, no one will ever be able to do it as well as you do it because it’s not identical to how you did it! And we tend to fixate on silly little things that don’t have as big an emphasis on quality as we convince ourselves they do. It’s just how the brain operates!
I had a client lately who was trying to re-insert herself into her business because of a similar mindset. I asked her why she was doing that when she had started working with me specifically because she wanted to step away from the business more and more. Her response was “I don’t want the business to fail!” So I asked her how strong the business was and how well it would be able to weather storms if it constantly relied on her to NOT fail. It caught her off guard and she realized that she was playing up a couple of issues and re-inserting herself in her business unnecessarily. It was a different way of saying “If you want something done right, do it yourself” by reframing it as “I am the only person who can keep this business from failing.” But it was just as dangerous and the moment she stepped back and realized it, you could see her tense shoulders relax, she smiled again and we were able to work through how to empower the team to take charge so she could stay in the backseat and they could keep running the business while she focused on her new venture.
Thank you for all of that. We are nearly done. You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
My goal is to create awareness across the globe about the power of personal choice. When we can get people to internalize their choices, and their results, and understand that they have a LOT of control over their personal life, and they aren’t subject to their thoughts, to the whims of others or their environment, etc, it changes a person. When I realized that I had to stop externalizing what happened in my life and take control over it and take action, it rapidly propelled my life, and my happiness which allows me to live up to the impact I am capable of and I want everyone to experience this!
How can our readers further follow you online?
This was very inspiring. Thank you so much for the time you spent with this!