An Interview with Professional Photo Organizer Lisa Winningkoff

We are excited to introduce a new series of posts that will feature photo organizers whose stories are inspiring and their career transformations have resulted in them creating a profitable photo organizing business.
Our first interview is with profitable photo organizer Lisa Winningkoff.

1. Share your background and what led you to become a photo organizer?
I’m a CPA and after several years in public accounting as an auditor, I had a long corporate career working for a publicly traded deathcare company. While I started in accounting, over the years I worked in other financial roles, HR, compensation & benefits, training, compliance, etc., eventually being promoted to senior vice president and corporate secretary. Then the company was acquired by a larger competitor, and my position was eliminated. That gave me the push I needed to start thinking about my next chapter.

I always wanted to own my own business, but I wasn’t sure exactly what that would be. I started thinking about who I was (organized, logical and meticulous) and what I liked (problem-solving, continuous learning and creative pursuits), and I started doing research. I stumbled upon photo organizing and couldn’t believe this could be a career. I had enjoyed making photobooks in the past, and in my gut, I knew this was a great fit. I immediately dove in, immersing myself in all the information and training I could find and set up my business.

2. If this is a new career for you, what prompted you to reinvent yourself?
Job elimination is a pretty strong prompt, that’s for sure. Looking back, I definitely see that it was a blessing. Without it, I would never have had the courage to make a change. After some reflection, I knew what I did NOT want to do – endless meetings and conference calls, being responsible for 60+ employees, navigating corporate policies and procedures, etc. What I DID want to do was delight people by solving problems and making a real difference in their lives. Whatever the next act was going to be, it needed to be something fun that I could be excited about each day.

3. What was your biggest fear about offering photo organizing services?
I love training and continuous learning. No matter how much training I completed, I was always worried that it wasn’t “enough” or that clients would have questions I wouldn’t be able to answer. Guess what? There are questions that I can’t answer on the spot, but I haven’t died from it. The fact is that I do know a lot – and definitely more than what my clients know. Clients are impressed and so grateful when you help them in even the smallest of ways, and it’s very gratifying. I’ve also gotten totally comfortable telling a client, “That’s a great question. Let me do a little research and I’ll get back to you.” We don’t expect others to have answers to every conceivable question, so it is unrealistic to expect that of ourselves.

4. Are your own photos organized?
I’d say that my digital photos are about 90% organized, and my print photos are about 60% organized. The prints have been scanned, but the originals are not as organized and accessible as I would like them to be. Art and school work from my children (now 23 and 20) have been pared down significantly, and my next project is to digitize those items and then create some photo albums. I don’t think I need to save a necklace made out of pasta for another 20+ years!

5. What is a big (or small) mistake you’ve made and what did you learn from it?
“If I ask you what time it is, don’t tell me how to make a watch.” Have you heard that one? That was me. I was prone to giving clients too much information – in person, on the phone, in email updates, etc. It was overwhelming to them and time consuming for me to prepare so much information. Honestly, it was also a little deflating when they didn’t react with excitement over some long bulleted list of tasks accomplished. I needed (and got) a reality check. Listening, connecting and engaging were much better than inundating clients with too many details. Now I keep most of the details to myself (unless asked, of course, and then I will happily provide more information!) and instead wow them with snippets of information or some fun photos I’ve found. That translates to more enthusiastic reactions and faster payments on invoices. Jackpot!

6. Best client success story…
I had a digital photo organizing client whose aunt passed away. The client was making the funeral arrangements and planned to gather the family at her home after the services. She texted me to ask how to gather photos of her aunt that she wanted to display on her digital frame. I told her, “I can handle this for you.” She initially objected, saying she didn’t want to bother me, that it would take too much time, and that sort of thing. Fortunately, I had set up a Nixplay digital frame for her and had access to her account. In less than 20 minutes, I searched her collection, gathered the best photos of her aunt and loaded the playlist to her frame. I texted to ask if she could see them, and she was thrilled. It was a huge relief to her and something she no longer had to worry about. A few days later, she texted to say how much everyone enjoyed looking at the photos. Without an organized collection, this wouldn’t have been possible. Being able to help a client – especially under those circumstances – is the best feeling in the world.

7. What training from Sherra & Rita has helped you the most?
I believe I’ve invested in all of the training Sherra and Rita offer (I told you I love training). The earlier courses on “hard skills” like DPO (Digital Photo Organizing) and Photo Mechanic really laid the foundation for my technical skills and workflow. I still use them as resources as needed.

Without a doubt, it was the Profitable Photo Organizing (PPO) course that focuses on “soft skills” that has helped me the most in my business. The impact has been tremendous. With a focus on identifying ideal clients and the language choices that help you connect and engage with them, the PPO course has been a real game-changer in terms of consistency and profitability. My roles in the past have been technical, so it’s been a challenge to soften that language when speaking with clients and potential clients. I love that Sherra and Rita provide specific examples so that I can feel relaxed and prepared.

8. What services are most profitable for you?
Digital photo organizing is my most profitable service and where I spend the majority of my time, followed by print organizing and scanning. I would like to move into more album design, and perhaps some of the clients with whom I’m currently working will get to that point.

9. Best tip for a new photo organizer…what you wish someone would have told you sooner?
Remember that you are not your ideal client. What matters to you, like knowing all the details of how something works or sticking to a budget of $xxx, may be of no interest or concern to your ideal client. Think about that in terms of your website and communication style. Who do you want to attract and work with? Every client I’ve worked with simply wants to know their project is in capable hands and will be completed by someone they know, like and trust. Be that person!

10. Anything else you want our readers to know?
You can absolutely do this! You need to get out there and find that first client … or find a few more if you’ve already found the first one. It’s time to stop hiding at your desk trying to do “just one more” technical training course or buying “just one more” piece of equipment or software. Finding and working with your ideal clients will be a huge boost to your confidence, experience and of course, profitability. No technical training, software or equipment can ever compete with that.