The Trusty Oak Blog

This Coaching Software Helps Us Work Better Remotely

When I started working remotely as a virtual assistant, I’ll admit I wasn’t an instant success. 

I was new to working remotely and while I was confident in my skill set, I was finding it difficult to connect with my clients. One of my first clients was an entrepreneur who had a thriving one-person company. He worked long hours and couldn’t be bothered with emails or project management. Let’s call him Bob. 

I liked Bob: he was personable, relaxed, and engaging. We had good phone calls. The problem was our phone calls were never productive. I struggled to get Bob to delegate things to me: he was disorganized and distracted. He spent a lot more time telling me stories about his customers (who he was clearly brilliant at engaging with and selling to) than letting me login and update his customer relationship management system

Related: Mastering the Art of Delegation

In the end, Bob and I weren’t able to make our relationship productive. We just had a lot of nice phone calls. If I knew then what I know now, I’m confident I could have helped Bob clean up his CRM, automate his billing process, improve his customer service, and maybe even scale up his business. What I’ve learned about remote connection and how various personalities develop relationships virtually has made all the difference. 

Relationships Take Time

Bob was a relaxed client who wanted me to manage things for him. I didn’t know that and kept waiting for him to tell me what to do and when to do it. There are probably dozens of other things (at least) that I didn’t know about his communication and leadership style. We may or may not have been a good match personality-wise—I didn’t get to know him well enough before our relationship ended mutually. 

Today, there are a lot of things I’ve learned through years of experience and lots of trial and error. I’ve learned you need to get to know your clients and co-workers in a whole new way when you’re working remotely, and that communication is even more critical in a remote setting than an office. 

I also know that learning about someone takes time: sometimes, it takes valuable time that also should be spent on getting things done. That’s why one of the tools our team started using in 2020 has revolutionized how we work together remotely and made us a better team, better at helping clients, and more aware of our own strengths and weaknesses. And best of all, it’s already seamlessly integrated into our day-to-day work life. Let me tell you more about it.

How Cloverleaf Works

The tool we use is called Cloverleaf, a platform that “provides ongoing insights and coaching tips that fit effortlessly into your team’s workflow.” Here’s how it works.

Every day, when I log into my inbox, one of my favorite emails to open is from Cloverleaf Coaching. Today’s tip, for instance, told me this about myself: 

(Image: Screenshot of Emily Fisk's Daily Coaching Tip From Cloverleaf)(Image: Screenshot of Emily Fisk’s Daily Coaching Tip From Cloverleaf)

Cloverleaf also integrates with my calendar and will deliver tips about people I’m in meetings with each day. For example, last week I had a meeting with a client and a virtual assistant. Cloverleaf came through with a handy tip that proved invaluable in understanding each individual in the meeting. 

Image Screenshot: Daily Digest Tip from Cloverleaf Platform

(Image: Screenshot of Daily Digest  Calendar Tip from Cloverleaf)

How did Cloverleaf know this magically helpful information? Through personality, communication, and work style assessments we ask our clients and virtual assistants to take. 

Commonly accepted assessments like DISC, 16 Types (sometimes called Meyers-Briggs), StrengthsFinder, and more all combine in Cloverleaf to create a surprisingly comprehensive map of each individual in your team. This profile becomes incredibly useful for getting things done and working together effectively.

Besides the daily coaching tips and calendar digest emails, you can also integrate Cloverleaf with your Slack team for customized prompts. For instance, Cloverleaf might prompt you to reflect on a time that a particularly detailed-oriented team member helped make a project better by dotting every i and crossing every t. I love this part of Cloverleaf in particular: celebrating each other’s unique strengths and contributions is a great way to build team morale and connectedness. 

How We Use Cloverleaf

Today, Cloverleaf is a part of my everyday work routine and I’ve found amazing value in it. Particularly as our remote team grows, Cloverleaf has become a foundational way I get to know team members who I don’t have the luxury of seeing in person every day. We add each new virtual assistant to our internal team as well as a smaller “team” with their client so they can do the same interpersonal work that we do internally. 

We’ve found Cloverleaf useful in an impressive amount of ways. 

Team Building

When working remotely, opportunities for team building are limited. I love working remotely and wouldn’t trade it, but I’ll also be the first to admit that it comes with a list of cons as well as pros. The fact that after-work happy hours are all virtual is one of them (and other traditional activities that build team cohesion). Cloverleaf provides an opportunity to get to know each other in the virtual environment faster, better, and more effectively. 

Resolving Conflicts

When I have a tough conversation coming up or am feeling myself get frustrated with a teammate, the first place I go these days is Cloverleaf. I can read each person’s profile and look for clues to help me understand where they’re coming from and even compare my communication style with theirs. This is absolutely invaluable when I’m working toward mutual understanding and resolving any conflicts: I have a tool in my pocket that helps me gain insight into my teammate’s desires, needs, fears, and work style.

Image Screenshot of Amber Gray and Emily Fisk's Profiles from Cloverleaf Platform

(Image: Screenshot of Amber Gray and Emily Fisk’s Profiles from Cloverleaf )

Clients and VAs have access to the same information, and I know from firsthand experience that VAs use this knowledge of their clients to make partnerships stronger and more effective. 

Communicating Effectively

The other way that Cloverleaf helps me and our virtual assistant team work together is through understanding each others’ communication styles. For instance, some team members have blunt and to-the-point communication styles: a strength when facts and honesty are needed. But for others, this style can come off as cold or unfeeling. Of course, the opposite can be true as well: individuals who prefer straightforward communication may be annoyed or confused by the more passive, quieter communicators. 

Understanding is the beginning of empathy, so gaining insight into each others’ styles of communication is an enormous value-add. This kind of information can head off confusion, strengthen team bonds, and simplify projects in dynamic ways. 

Connection Can Happen Remotely

Going back to the story I told at the beginning of this blog post: I know I could have been more effective for Bob. There were a lot of things I have learned about working remotely over the past several years. But I can say confidently that Cloverleaf would have helped me. I wish I had more insight into Bob’s personality and his strengths and his weaknesses as a delegator. I wish I could go back and take the lessons I’ve learned and have a do-over. 

Of course, I can’t—but I can continue to learn from the incredible insight that Cloverleaf is serving up to me in digestible tidbits every day. Cloverleaf has strengthened my conviction that connection can happen remotely and that remote teams can be just as effective as traditional teams. 

Maybe Cloverleaf can make the difference for your remote team this year. 

Ready to see how a virtual assistant can help you? Start a 90-day trial today!

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Emily Fisk

Emily Fisk began her career in marketing after graduating from Boise State University with her B.A. in English, Rhetoric and Composition. Emily started freelancing as a writer and found Trusty Oak in 2016. Emily spent three years as a virtual assistant, helping clients build their digital marketing efforts, while taking on more responsibility as an account manager and marketing manager as Trusty Oak grew. In 2019, Emily took on the role of Marketing Director, and in 2020, she began serving as Trusty Oak's Vice President of Operations. Emily’s passion for clear communication, vibrant teamwork, and helping others find meaningful careers has made her a key part of Trusty Oak’s growth. She gets a kick out bringing Trusty Oak’s story alive and watching clients succeed. Under her leadership, the Trusty Oak marketing team has accomplished large-scale projects and numerous successful campaigns, undertaken new brand identity initiatives and launched innovative content. When she’s not working, Emily loves digging into a good book, cooking a delicious meal, and getting outside with her two daughters and husband. She lives in beautiful Boise, Idaho and is a founding member of a (totally cool, not at all nerdy) writing group.