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How One Entrepreneur's Vacation Fixed A Small Business Crisis

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When she first launched Student Maid, Kristen Hadeed would create long, comprehensive to-do lists for all her employees. Student Maid is a cleaning and concierge company, but not your typical cleaning company: they only employ students, helping team members grow into self-managing professionals who value flexibility, accountability, and autonomy.

With the best of intentions, Kristen says she was doing all the discretionary thinking for her millennial employees at the time: “I would also then make myself available, 24/7, to answer all their questions,” she says, which they had no shortage of at the time.

But, over time, running the company was becoming a treadmill she couldn’t take a break from, in many ways.

When she took what was supposed to be her first vacation since starting her business, disaster struck.

Photo Courtesy of Aileron

“The people I’d left in charge couldn’t get in touch with me [because I was on a plane]. When I made it back to the ground, I learned they’d handled the crisis completely on their own,” says Kristen.

The experience helped her realize they were capable of thinking for themselves, and solving problems on their own—when she gave them the chance. “I was the one getting in their way. By creating those lists and solving every problem for them, I’d made them completely dependent upon me,” she says.

Her strategy for delegating with her millennial employee base is now one that encourages the team to be independent, but it also makes them feel supported.

Here are 4 tips she has for delegating to help unleash the potential in employees:

1. At the start, explain the project as clearly as possible. “I explain the end goal of the project I’m delegating very clearly. I also make sure the person has all the context they need upfront, which could include things like budget, resources they’ll need, research they may need to reference.” This also includes setting a timeline and check-in dates where major milestones can be shown and questions can be asked.

2. Make a conscious effort toward empowering employees. During meetings, Kristen is intentional about not solving problems for employees. “In our meetings, I don't do any problem-solving. If they've run into an issue, I ask them to come up with two solutions, and I will help them choose which one to follow.”

3. Use the power of communication for greater alignment . Kristen’s found that communication is of utmost importance during this process. “To make sure we are on the same page, I’ll ask team members to repeat back to me what I’ve explained, to make sure they understand my expectations and the end goal. From there, it's totally up to them to decide how to reach that goal by the date we've chosen.”

4. At the end, encourage and make room for feedback. After they’ve finished a project, Kristen sits down with them to analyze what, if anything, went wrong and what went well. This feedback phase is vital to helping people grow, she says: “If they don’t know what they did wrong, they won’t know what to avoid doing next time or learn how to be better. And the same goes for what they did right: They need to know what they should keep doing.” Positive reinforcement is just as important as critical feedback , she says.

Photo Courtesy KristenHadeed.com

Walk the Line

When you have a culture that embraces mistakes and encourages personal growth, the difficult part can be you have to walk the line between being supportive and holding people accountable, she says. “Figuring out what that line is has been the biggest challenge in my own company, and sometimes it still is.”

When someone does make a mistake, Kristen says 3 things typically happen in her company:

1. Uncover what went wrong. If someone does mess up, be sure you address it so that all involved can learn and grow. Ask the person what they would do differently the next time around, and be sure to document everything so that you can reference it in the future in case the same mistake happens again.

2. Clarify ways to make sure the mistake doesn’t happen again. Kristen believes that it’s the organization’s responsibility to give people all the tools they need to do their job. “I always ask myself, did this person mess up because we didn’t prepare them properly? Are we at fault here? If so, we might need to give them additional training or clarify our policies. Or, is it something they did wrong? If so, you’ve got to push them to be better and hold them accountable.”

Training and development at Student Maid focuses on helping leaders build the skills critical for their long-term success, including how to manage difficult conversations, how to give and incorporate feedback, how to build relationships, how to problem-solve, and more. “We want our people to leave better than when they came in. We want to equip them to lead our world. That’s why our students buy-in to what we’re doing, because they know we are investing in them.”

3. After providing feedback and support, if someone is still messing up, it might be time for change. “After that, if the person keeps making the same mistake, we see that as a sign that they’re not really trying to learn and improve. It tells us they’re not invested in their growth as much as we are, so it’s probably time to part ways.” In many situations, that can still be a learning opportunity for that person.

On the other hand, if a person continues to make different mistakes, but is still proactively seeking to learn from her mistakes, the situation is different. “If the person is ‘showing up’ in every other sense—living our core values, following company policies, and their heart is in the right place—we are going to continue to help them. If someone is willing to try and put effort into learning and getting better, I believe it’s absolutely worth it to do everything in my power to help them.”

“As leaders, it’s our responsibility to create a space for our people to be successful,” says Kristen. “And so that requires understanding, ‘What does this person need to be more successful here?’ Then you’ve got to figure out a way to give it to them.”

This leadership shift has accelerated the company’s growth: not only do students line up to work at Student Maid, the company is thriving, they’ve opened a second location (which they have since sold), and Kristen has successfully handed over day-to-day operations to a leadership team comprised of millennials. She spends most of her time speaking to organizations around the country about how to engage the next generation and improve workplace cultures.

This is part two in a two-part series with Kristen Hadeed. 

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