I stayed with that coach for another little bit, though, until I realized that it was really, truly time for me to move on. It happened when I had a client who I’d worked with intensely on getting this family a home that would work. (I’d even pushed myself to a showing when I was sick and pregnant. When I fainted at the home I was showing, I got back up and continued giving them the tour.) Then one day, he called me with the words, “Thanks for your time, but we bought a property with someone else.”

Even though something like this happening is a normal occurrence in the real-estate industry, this time, it hit me particularly hard. I called my coach in tears. He listened for a minute and then said, “You know what, Mrs. Norman? You’re being too negative.”

It was the wrong thing to say. I was already crushed. What I needed was supportive advice and perspective that would help me work through this.

I shouldn’t have been surprised though. His response was the same bootcamp style I’d come to expect during our weekly meetings.

That was the last conversation I had with him.

Immediately after, I switched to a different coach who has a different approach. He has been a much better fit — some of it for very practical reasons. Yes, he has an overall different approach, but he also prefers to meet in person, which is much better for me. He’s a lot more hands-on and will even come with me to difficult client meetings.

I really knew I’d made the right move, though, when I ran into a difficult client situation a while later. After working a tough deal for a while, the client called to say that he wanted to reduce my commission. After how difficult they’d been? Absolutely not!

I called my coach and walked him through the situation. “You’re not going to reduce your commission,” he said. “You’re actually going to ask for more.” Then he walked me through the conversation I should have, guiding me on what to say and when. I went back to the client with a counter offer.

I smiled when he agreed to not to lower my commission, but to pay a higher one.

This is what I wanted a coach for.

Tehila Rosen, marketer

“I’ve spent $10,000 on coaching — but it was worth every penny”

I started working with a coach back in 2018, mainly because I wanted to make more money. I worked in marketing, and I had a mix of private clients I was working for, and a part-time job preparing marketing materials for a company. I was working so many hours and yet coming home with such a small paycheck. I remember my sister-in-law saying something about how she started davening Maariv, and I wanted to cry. How did she have time to think about taking on something extra like that when I was spending all my spare time working?

I scheduled my first free call with a coach after a friend recommended it. I got on the call and was immediately sold. (Later, I realized that that’s the point of these calls. Yeah, the coach is going to provide free value, but the main reason is because they want you to purchase a program or package.)

With my first coach, I had no idea what to expect or what I was getting myself into. Our sessions were transformative, but when I shut the computer after our sessions, I felt miserable. She was pushing me to do a lot of inner work on my mindset and on unblocking limiting beliefs, and I realized that while the work was life-changing, it was difficult emotionally, and I needed someone who would be more empathetic through the process.

I gained enough working with her to be sold on the idea of coaching, but we had an energy mismatch, so I knew I needed to switch.

The next time I looked for a coach, I was a lot more discerning. I did a lot more research into the personalities and styles of the coaches recommended to me, and only signed up for a package when I was absolutely sure it was a good fit. Baruch Hashem, my next coach really was.

She helped me with a lot of mindset work and unblocking limiting beliefs. And as I worked with her, amazing things started happening. I got more and bigger clients, and even bigger ones, well-known institutions and businesses. I had more offers for speaking engagements. I felt more at peace with the hustle of my business.

I started a new train of thought, which created new beliefs, which were the foundation for a new reality. My mindset wasn’t working against me anymore.

I felt like I discovered a magic bullet — this amazing secret. I think it’s a lot more than that though.

Yeah, it’s (very) expensive — especially if you take a good coach. But the experience was absolutely life-changing, and I’m not exaggerating. It’s an investment with the highest possible ROI (return on investment) because you’re not upgrading your software, which will eventually get outdated, or your team, who may move on. You’re investing in yourself. And you are your biggest asset. When I made the decision to get coaching, I created this shift that says, “I am Tehila Rosen and I invest in myself.”

I think people sense that I take both myself and my business very seriously.

The business will only be as strong as the business owner. You’re the leader and when you develop your skills, you develop your business.

—Sara Sicherman, business coach

Chava, service provider

“It just wasn’t working anymore”

Over the years, I’ve used a business coach mainly on an as-needed basis. If I was ever working on a high-stakes offer, like launching a new service, I would reach out for support on my strategy because these were big decisions about services that are worth thousands of dollars, and I was willing to pay top dollar. There were times I invested close to $1,000 for an hour of coaching, just to get another experienced brain to weigh in on the topic.

Often, what the coach did was simply give me clarity. She didn’t tell me what to do, but she’d give me a new framework or approach to the challenges. She didn’t make the decisions for me — she’d ask the right questions, shift my perspective, and then I’d make my own decisions based on those frameworks.

I think that’s the difference between coaching and consulting. With consulting, the expert tells you what to do. With coaching, they make the environment less foggy so you can come to conclusions on your own.

I much prefer coaching because — at the end of the day — no one knows your business as well as you do. I can’t say, “It’s directly linked to me making thousands more,” but it gave me an overall sense of what I should be doing next.

At times, though, specifically because I was paying so much, I was a little disappointed with my coach’s time management. She used to do some small talk at the beginning of every call, which is standard for getting into the swing of things, but frustrating when you’re paying so much. If you want to include this as part of your warm-up to the coaching, don’t include it in the hour. When clients are paying so much, they want the most of every minute, so you can chat for a few and then say, “I’m starting the 50-minute timer now.”

Even with being frustrated about that, I still used the same coach for years — until I realized it just wasn’t working anymore.

I would come off our calls and tell my husband, “I’m so drained.” It was strange because I’m usually a pretty energetic person and I love my work, so it usually enlivens me, but here I would talk about something I love for an hour and walk away exhausted. It just wasn’t like me.

I realized that our energies weren’t aligning anymore. My coach has a huge personality that takes over the room. I felt like her energy was so big and overwhelming that there was no room left for me. I would wither next to her and walk off the calls feeling like a wilted wallflower who could barely get a thought out.

Sometimes, it felt patronizing. I would ask a question and she’d say, “I’m going to tell you something that will change how you think about it so you never have this question again.” She was trying to be helpful and give direction, but I felt patronized, even a little stupid. But at the end of the day, if I’m able to pay $1,000 for a coaching session, I’ve clearly achieved some form of financial success. I’m not a complete idiot about running a business — and I wish she would have had more respect for that.

There were also times when I felt like she was the hero instead of me. When I’d bring up a concern, she’d address it by sharing a story that happened to her and how she dealt with it. Sometimes that helps you make a point, but it’s not always necessary — especially if you go on for too long. I came to talk about me and my business, not to hear about yours.

Looking back, I don’t think her coaching approach changed. It’s something that was encouraging and helpful at the beginning, but as I grew more confident and more self-aware, I was less keen on it.

Our energies didn’t align anymore.

Circumstances change and hopefully people change, too. Ideally, though, you should be able to make sure it’s a good fit from the start. Coaches offer free calls, so take advantage of those. Personally, I think coaches should offer more than one if someone’s not sure. Coaching is a long-term commitment and you don’t want to be locked into something that’s not a perfect fit for you. Take as much time as you need so you know that this coach is the right one for your stage of business, for your personality, and for your long-term goals. If they’re not, you’ll feel like you wasted your time.

—Sara Sicherman

Istopped booking sessions with this coach, but I still don’t regret all the times that I did. If you’re dealing with high-stakes decisions, it’s important to get a third-party opinion on the things you might have missed. Without that, you run the risk of making mistakes with serious and expensive repercussions. And with it, you have the clarity and insight that only someone outside your fishbowl can provide.

Estie, e-commerce owner

“All we wanted was to gain from the time and money we were investing”

Irun my business in partnership with two other friends. We started almost by accident and, baruch Hashem, things really took off. About two years in, we realized that we were expanding so fast that we needed support. With three people, there are always three opinions on what the next step should be. We wanted to get an expert’s insight to help us move forward.

We did our research for a while and kept hearing the same name on repeat. Everyone said this coach was life-changing, so we booked a free call. By the end of it, she’d sold us on a $400 coaching session. Two of them, actually. She wanted us to book back-to-back so that, with so many people on the call, we’d still be able to make headway.

We laid out the $800 to book. It must be worth it, we figured. Everyone said she’s so good.

Two hours later, we were nowhere. The coach showed up to our call completely unprepared. She didn’t know what we did and spent a lot of time asking basic questions that are either common knowledge about our industry or that she should have remembered from the free call.

When we hung up, we looked around at each other and asked, “What did we actually cover during that call?”

No one could answer. It felt like we’d made no progress at all.

When we raised the concern with the coach, she sold us on a $10,000 coaching package. We heard everyone’s recommendations in our heads — “she’s the best” — so we booked, even though we’d already invested and still hadn’t seen value.

Before our next session, we were already having cold feet. If we didn’t get anything out of the $800, why would paying more than ten times that help?

“Can we hear the recording of our first session?” we asked the coach. We figured we’d go through it again to listen with complete focus and pick out all the gems we were supposed to have gained.

Radio silence. The coach didn’t answer any of our emails.

After a week, she finally responded — apparently the recording had been deleted.

We paid so much, we told her. Could she at least give us a recap of the takeaways?

Instead, she refunded our money. To be honest, that isn’t what we wanted. We didn’t want our money back. We wanted value.

The coach probably thought we were being difficult, but all we wanted was to gain from the time and money we were investing.

After the saga, someone gave us advice I wish we’d had from the start: “You need to know what you need.” Are you looking for a cheerleader? A therapist? For a lot of business owners, that’s the goal. In our situation, we work as a team and already have the built-in support. We wanted expert guidance — and I think that’s why the coach who everyone so highly recommended wasn’t a fit for us. She works with business owners who need someone to listen and give encouragement. We already had that built in to our business model. She might be great for someone else, but she’s not for us.

We needed to know — were we looking for financial guidance? Marketing support? Hiring assistance?

Once you have the answer, then you can look for someone who helps with that specific field.

After speaking it over with a few people, we realized that we needed help with one specific area — finances. We hired an outsourced CFO who came down to do an audit, found our holes, and helped us patch them. Since then, we only hire people who specialize in a specific area and who have a clear process. We’re not looking for an endless arrangement — it has to have a clear beginning, middle, and end. That’s how we make sure we’re making the most of every dollar we spend.

MAXIMIZING THE COACH-CLIENT RELATIONSHIP

If you’re thinking about hiring a coach, make sure you’re making the most of the relationship. Here’s how:

MAKE SURE YOU’RE READY

Some people rush to invest in coaching from the get-go, but it’s not always the smartest idea. “You need some experience, some stamina, and to be roughed up a bit before you can make the most of the relationship,” says Nechama Norman, a real estate agent from Lakewood. If you don’t have any business background yet, you won’t appreciate the coaching — and it might become a crutch. You won’t believe in your ability to do things on your own. And you might not actually be able to.

Nechama recommends absorbing all the free information you can first. If you’re starting in a new industry, read books, watch videos, and speak to people in the field. Once you feel like you’ve taken everything that’s available for free — and think you need more one-on-one guidance — then it makes more sense to invest.

Sara Sicherman, a business coach with 20+ years of experience, agrees. “To get the most out of coaching, you have to be at the stage where you’ve already found your limits — and now want to break them. People who are the best fit have usually achieved some success already and are now experiencing growing pains or feel like they’re maxed out.”

KNOW WHAT YOU NEED

Nechama realized pretty early on that she wasn’t looking for a cheerleader. “I have those in my personal life already. I didn’t need to pay for someone to give me a pat on the back. I wanted to pay for someone to give me insight and better ideas than I could come up with on my own.”

It’s important to know the difference between a coach and consultant — and to know which you need. If you invest in the wrong one, you’ll likely be frustrated when they don’t help you reach the goal.

CHECK FOR EXPERIENCE

“Coaching can never be a person’s first job,” says Sara. “You need first-hand business experience before you can support anyone else.”

On top of general experience, sometimes you need someone with niche expertise, too. Nechama likened it to a retail shop owner hiring a coach who only has a background in graphic design. “If your shipment gets stuck at the port, they won’t have any helpful advice for you. You need someone who also has retail experience, can understand the repercussions of every decision, and who has practical advice — like do this or do that to get through it. How can they coach you through your challenges if they don’t actually know them?”

She also recommends checking references. “Coaches should be able to offer you references,” she says. “And if they can’t, chances are they’re not going to be a good fit for you.”

DO A VIBE CHECK

“You have to click with the coach you’re investing in,” says Tehila. Many offer free calls, so schedule those to feel out the experience — but go in with an open mind. The goal of that call is to “sell” themselves to you, so be critical. Don’t get swept up if you’re not ready and if anything feels even slightly off to you (even if it’s just a personality thing), don’t rush to make a commitment.

“When you get off that first call, you want to feel good about yourself,” says Chava. “You need to end every session better than when you started. If you don’t, that’s a red flag.”

PUT IN THE WORK

“A coach can’t do anything for you,” Estie points out. “They give guidance and you have to follow through on it.”

“It’s not an easy way out,” Tehila echoes. “It’s actually a lot of hard inner work. Most of it actually happens after the sessions, and if you’re not ready to face that, you won’t get much out of your time together.”

Nechama points out that there’s no secret sauce. “Everyone has the same recipe. The difference to the final ‘dish’ is how well you follow the directions. When you hire a coach, they give you a recipe. You need to be ready to work.”

REMAIN EMPOWERED

Chava stopped coaching when she realized that she was losing herself in the process. It’s not an uncommon phenomenon — and one to look out for.

“A coach is an expert in their field. You’re the expert in your life,” says Tehila. “You must remain empowered. If they say something that’s not comfortable to you, call it out. Be willing to push back if their advice feels wrong for you. You have to make sure that’s always the dynamic of the relationship, and if that shifts, it’s time to reevaluate.

“You don’t always have to take a coach’s word,” Sara agrees. “If a coach imposes their take on a business or a client, I wouldn’t trust them. Don’t follow blindly when someone is clearly pushing an agenda. A coach can say their piece, but they can’t push it. You know your business best, and you’re also the one taking all the risks. You have to make the final decision because you’re the one who has to sit with — and be comfortable with — the ramifications.”

(Originally featured in Family First, Issue 901)