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EP 140: Paying Attention To The Red Flags With Don’t Panic Management Founder Jess Ostroff

The Nitty Gritty

  • The red-yellow-green system Jess Ostroff and the Don’t Panic Management team apply to every potential new client relationship and new hire to help them take the emotion out of it, particularly when it’s not the right fit
  • What Jess does if a potential client isn’t ready for their services yet, like helping them systematize their business so they’re ready for an assistant in the future
  • Why Jess chose to only hire United States-based and college-educated virtual assistants

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This week’s guest is Jess Ostroff, founder and Director of Calm at Don’t Panic Management, a people-first virtual assistant agency founded in 2011. In addition to running the Don’t Panic team, she’s also a speaker and author of Panic Proof: How the Right Virtual Assistant Can Save Your Sanity and Grow Your Business.

In this episode, Jess shares the process she uses to vet new clients and new hires, plus how she operationalizes red flags to help her identify make-or-break situations using a red-yellow-green system. For Jess, this system helps her make choices that are informed by both her gut reaction as well as objective facts.

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Operationalizing red flags

“It’s not just feeling. That’s why we have this red-yellow-green system. I might say: Sally is so nice and she really needs our help. And Jen, my colleague, will say: yes, but did you see those 10 red flags? We gave her a yellow and now she’s a red. She’s not a good fit for us. It makes it easier for me to say no with objective ranking factors in place.” — Jess Ostroff

How many times have you said yes to a new client when you should have said no? Maybe the client needed more than what you offered but you felt bad or felt like you should say yes simply because you knew you could help them (and you needed the work.)

Whatever the situation, Jess’ method for systematizing red flags with new clients is key for looking through an objective lens rather than a rose-colored one. “I like to start out by feeling what I’m feeling,” says Jess. “But then I like to fact-check that against that everything else I have in terms of information.”

Here’s a real-life example. The beginning of a new relationship with a client starts with a general form on Jess’ website. Once they receive that email, they apply the red-yellow-green system immediately. They only move forward with people who pass with a yellow or green.

Here’s what this looks like:

  • Red is a hard no. If the individual provides no information about their business in their initial email or there are other indications that they aren’t a good fit, they don’t move forward.
  • Yellow is a maybe. In this situation, Jess would need to gather more information. She might ask them to fill out a pre-call form to get a feel for their experience working with assistants, plus what their needs are.
  • Green is a yes. These individuals are self-aware, very organized, and very communicative. It’s obvious that they’re ready for the help and they have a system for bringing on an assistant with clear tasks and expectations.

But the red-yellow-green system doesn’t stop at the intake form: it’s used at every additional step, including phone calls, to ensure it’s a good fit for everyone. “If it’s a red, I’ll say: you know what, I don’t think you’re ready or the right fit,” Jess says, “and I’ll point them in another direction.”

Finding and working with clients that are the perfect fit

“I want to work with people who really, truly understand the value of their time so then they respect the value of our time.” — Jess Ostroff

Using the red-yellow-green system, Jess finds out who’s not a good fit or if they aren’t quite ready yet. “I really have to say no if they’re not ready because we’re not going to have a successful relationship,” Jess says. “I don’t want to work with someone for two months. I’d rather develop a long-term relationship.” And the system is working. Many of Jess’ clients have worked with her for ten years.

So how does she maintain that longevity in a world where virtual assistants are incredibly easy to come by? She hires only US-based employees that are college educated. Then, using an audit that shows where clients can delegate out, Jess pairs them with the perfect assistant for their needs.

But it’s not all about what Jess and her assistants provide. It’s also about working with clients who understand the value of what they offer. If people want to pay less, they can do that by hiring somewhere else. As Jess says, if her clients understand the value of their time, if they’re respectful, and they have an idea of exactly the tasks they need to delegate, it’s a good match.

Hiring the right people who align with your vision and values

“Reputation is the biggest thing for me. Most of my clients are from referrals and word-of-mouth. That’s because we have a positive relationship and I’m not willing to compromise on that.” — Jess Ostroff

Jess doesn’t only use this red-yellow-green system with new clients. She also uses the same approach when she’s hiring for her team. The interview is the first step. If a candidate gets a green on the interview, then they’re sent a test project with an objective grading process.

This entire process helps Jess find the perfect people who share similar values. For example, one of the values at Don’t Panic Management is Be Neighborly. Helping with a light and open heart is baked into everything they do at the agency.

Team members use a private Facebook group to connect on family life, hobbies, and so much more. That connection spread far past the employees. They form deep relationships with clients, too, because Jess prioritizes and systematizes a process that supports them.

Hear more from Jess Ostroff on operationalizing red flags in your business, working with the best suited clients, hiring people who share your business values, and so much more in this episode of What Works.

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EP 299: How To Design Your Own Sales System

EP 299: How To Design Your Own Sales System

This week, I’ve got 4 more stories to share with you from small business owners who have intentionally done things their own way when it comes to sales and selling. They’ve found what truly works for them–even if it bucks the prevailing wisdom or would make a bro marketing expert role his or her eyes.

These stories come from business coach Ashley Gartland, marketing expert Amy Lippmann, designer Mel Richards, and work reinvention coach Lydia Lee.

Listen for how they incorporated these same considerations into finding their own unique sales systems. They designed their systems with personal values, strong relationships, reduced anxiety, and agency in mind.

EP 298: Creating A Less Harmful Sales System with Wanderwell Founder Kate Strathmann

EP 298: Creating A Less Harmful Sales System with Wanderwell Founder Kate Strathmann

This show is called What Works for a reason.

Sometimes it’s a declaration: this is what worked for this small business. And often, it’s a question, “What works?”

Today’s episode is very much a question, many questions, really:

What works when it comes to selling when you want to avoid manipulative or exploitative practices?

What works when your values conflict with many of the best practices of selling online but you still want people to buy your stuff?

What works when it comes to sales in a business that is actively anti-racist and anti-capitalist?

And even more bluntly: Can you even sell things without causing harm or perpetuating harmful systems?

My friend Kate Strathmann is the founder of Wanderwell, a bookkeeping and consulting firm that grows thriving businesses while investigating new models for being in business.

Recently, Kate took a bit of a detour from how she’s used to building her business, which is 90% referral based and fueled by deep relationship- and community-building. She decided to offer a small group program called the Equitable Business Incubator as a way of exploring anti-capitalist business practices and how they apply to the small businesses we’re building.

To fill the program, Kate need to sell differently.

Which led her to asking the question: Can you even sell things as a anti-capitalist?

While that might not be your specific question, I have a feeling that you too have wondering how you can effectively sell your offers without causing harm, perpetuating harmful systems, or damaging relationships. And that’s why I knew Kate and I needed to explore this topic on the show.

This is a conversation about what a kinder, less harmful sales process could look like—and it probably contains more questions than answers. But I’m confident those questions can help you find the answers that are right for you and the sales system that you want to build to make your business stronger.

We start out by defining what we’re really talking about when we talk about capitalism and anti-capitalism. Then, Kate shares how the Equitable Business Incubator came to be and how she ended up selling it. And then we dig into what makes many of the sales formulas and best practices being taught today problematic—and how to think differently to create your own alternative practices.

Now, let’s take a look at what works for creating less harmful sales systems!

EP 297: Selling A New Program With Proof To Product Founder Katie Hunt

EP 297: Selling A New Program With Proof To Product Founder Katie Hunt

Today’s guest is Katie Hunt—who is a member of the former group and serves the latter group.

Katie is the founder of Proof To Product, which helps creative entrepreneurs run and grow thriving product-based businesses. She works with designers, illustrators, and artists to help them develop in-demand product lines and get them sold in stores all over the world.

Not long after the pandemic threw her business and the industry she serves for a major loop, Katie and her team launched Proof To Product Labs to provide a completely digital, ongoing support opportunity for business owners when they needed it most.

And that launch was a smash.

Katie and I get into all of the nuts and bolts of how she adjusted the offer to meet the moment and how she warmed up her audience before the campaign, as well as the exact mix of emails, podcast ads, and social media content she used to sell the offer when it went live. We also talk about how she sees the sales system evolving in the future and how the offer has been received now that people are using it!

What Works offers in-depth, well-researched content that strips away the hype of the 21st-century economy. Whether you love the podcast, the articles, or the Instagram content, we’d love your support.