Hiring – especially for the first time – can be one of the scariest moves as an entrepreneur. Rapport currently has nine crew on top of me, and the dog. I’ve had a lot of experience with this and, though was lucky to find really great people, learned a few things along the way.
This is one of the top things other entrepreneurs ask me for advice on. My top tips are:
- Try prospects out on a project or two before committing.
- Define the need/position first, then find the right person.
- Personality and ‘fit’ into culture is as important as skill.
- Be open to them doing things differently then you and let them shine.
Try People as Freelancers Before Hiring
My very first hire was Art Director Lisa, who is still with me today. I absolutely could not have built the company without her. I was fortunate to work on a project with her old boss and friend of mine
Mondo Lulu, and got to know her through him. Then, as he started scaling back she began freelancing for me. I knew her design style, her work ethic, that her strengths complemented mine, and that we got along like old friends. My only hesitation hiring her full-time was sustaining her pay. When I had the need with a large project and knew I could keep her busy for three months I asked her to come full time – that was six years ago.
Since then I’ve been fortunate enough to try most people out on a contract basis before making a commitment. Not just to see the quality of their work, but to get a taste of their working style and personality. If it doesn’t work out, it’s tough on both sides, so this is a really great way to try each other on for size.
What Kind of Help Do You Really Need?
My second hire was a newborn designer, and a big mistake. I was still doing all the admin work myself and felt I didn’t have enough time to do all that and my design work. I thought I needed another designer and the recent grad was cheap. I found I still didn’t have time to get anything done
and was also now babysitting this kid. So, I let him go and hired an administrative person. Pamela was a God-send. This was my first pure overhead employee – unlike Lisa who generated revenue. But, Pamela took the work I liked least off my shoulders, did it better than me and freed me up to do what I was really good at and made good money for.
Besides hiring for the wrong role, it’s also a mistake to hammer a job around someone you ‘like’. I now determine what roles we really need to fill against goals for the company, then create detailed job descriptions around them to use in my search.
Don’t Underestimate the Power of the Culture You’ve Built
Our team recently did a colours test with our business consultants, Your Planning Partners. Seven out of 10 came in as blue or the ‘Relationship Way’ first. We varied on what came second (Action, Organized, Logical), and that was reflected in skills and roles. What it told me was the team strongly embodied the Rapport values of being laid-back, friendly, relationship-oriented, client-focussed and a close family that got us our name. This culture started with me, gained
momentum with early people like Lisa, and continues today in the people we attract. Skills in relation to the role you’re filling are incredibly important, but if a really talented person doesn’t fit our friendly, collaborative culture they don’t belong at Rapport.
It’s important to have more than one of you meet with prospects. From a practical standpoint, I had Senior Web Developer Noel, do initial interviews with junior web developer prospects to make sure he had the skills needed. Then I met the recommended finalists to make sure they fit in and talk money. We added the ‘social interview’ with new guy Nick, where he joined the crew for drinks to get everyone’s feel for him. We are a very social bunch, and it’s a very big deal day after day if someone just doesn’t fit in socially. I think I’ll continue that tradition.
Define Your Values, Be Open to New Things
There is always more than one way to skin a cat. I find this most evident with web developers as their logical nature means they always question the way the other guy did it. But, it’s the same with design, processes and which way the toilet paper goes on. It’s important to define the standards expected for the end result as well as the practical processes that run the business, than make these consistent across the board. However, you’ve hired people to complement what you do, let them. This may mean everything from different journeys to great design, to suggestions that improve workflow.
We’ve defined our vision, mission and values, which I share with the company repeatedly. Resulting details include things like design and web standards, or the project management process we’ve developed. The key is sharing it with the whole team, getting their input, then giving them flexibility within to do their thing.
This makes for a much stronger and more dedicated team than if I insisted everything was done my way.

feedback. He got so many and such varied responses his head was spinning and couldn’t sleep that night.
take a specific action at the end? That it builds a feeling of trust and stability or makes people feel warm and fuzzy? Use this as a guideline to come up with specific questions. Like, ‘did it make you feel warm and fuzzy?’ Same goes for concerns you have – ‘or did it seem too corporate’.
input. Don’t be reluctant to ask – most people feel privileged that you value their opinion.
Except those same experts are often getting paid $500- $1,000 an hour (or more) to do client work. And if the marketing budget includes internal time…things can get really expensive, quickly. Or if the professionals in the firm don’t think blogging helps build business, the challenges can be even greater.
one of the most easily accessible lines of communication a company has, providing exposure to people that actually care about what your experts have to say. People that could easily become future clients.
outsource). Get your support team to find appropriate pictures. If all else fails, have your expert verbalize their opinions and have someone else write them down. Don’t forget to enhance the blog for search. That too can be outsourced.
y last employer (now a competitor) after the dot-com bubble burst. At the time I was totally devastated and just looking for another full-time gig. A couple people suggested freelancing, and I thought they were nuts.
il, he asked me to come right away and stay the afternoon if he liked me. He liked me, I stayed, he had me back a couple more days. Then he made a proposal – if I was there and available to him (and only paid) as he needed me I could use the space and equipment for free to start my own business. I actually said no and did a short stint at a large agency, but left after only a week because I just didn’t fit there.
for five years and serial board member) amongst others. I even started co-hosting a networking event which I found I loved. I had no idea that I was such an extrovert and loved meeting people. I had also discovered a great new peer group, who were not only in the same boat as I, but had the same underlying drive and guts that made us entrepreneurs.
d they start ignoring it. Meanwhile, if they also see an ad, an update pops-up on LinkedIn, then notice you’re speaking as an expert, or spot your brochure on a colleagues desk, then get the newsletter again; suddenly you are top of mind for whatever you do. Plus, you provide more opportunities for them to sell you to decision makers and more ways to refer you (ex: send your newsletter to a peer). You provide more opportunities for them to see your brilliance and understand all of what you do.
s great for bringing people into your funnel – the most fun projects for Rapport actually. However, if you succeed in bringing people in, then what? You need to have other points of contact ready to go to keep them engaged and coming back, or leading them to your pre-sale action step. For this particular client once she brings them in en masse, she needs to build trust with them to move to the next step in the buying cycle, so we have to make sure mechanisms for doing that are there to support the initial big effort.
to do and then plan and budget for them over a quarter, if not a year. An action plan really makes things much less daunting.
Terri suggested in her post 

– the hidden opportunities for business, jobs, friends and ideas happen become much easier to find. Just by sharing information on a social media platform, you have much more opportunity for being heard by this invisible network.






