Entrepreneurs ask me what’s one of the hardest parts of running a business and I always respond, hiring.

—Sevetri Wilson

Hiring and Finding Freelancers and Others

I've had some major wins with hiring. Those individuals I remember the most, their strengths, weaknesses, how we interacted and worked best together. What they brought to the team, the extra effort, the long hours, the willingness to step up when needed. So many different things made the individuals extraordinary at their roles respectfully. Yet, I'll also remember every time I got it wrong and why. Not a culture fit, the individual may have embellished their experience and couldn't perform once the time was needed, they doubted their work more than they should have. They stopped showing up not physically but they mentally clocked out and were not focused or perhaps they felt some work was beneath and was always waiting on someone else to do the job. Hiring is difficult yet, ultimately it will depend on your skills at (x) finding and (y) managing each type of resource. When people ask me what challenged me most early on, I say it was hiring. Hiring is hard. Over time it gets slightly easier, but not much.

When I hear from early-stage founders it's often to get my opinion on outsourcing various roles for their company, and if the founder is non-technical (meaning they can't themselves code or build their product), the question is always how I found engineers in lieu of having a CTO or hiring someone full-time. How do you get a freelancer or contractor to fully “buy in”?

In an ideal world, you'd get the cost-saving benefits of outsourcing along with the eagerness and real-time collaboration you get with a full-time hire sitting next to you, but in reality that combination hardly exists.

Generally, whoever is managing development at your company has experience in one of the two areas more than the other. If they are actually good at, and experienced with, managing a team in say, Ukraine (which is where we outsourced dev at one point), then it will probably work great. If they've never done this, but are instead used to working with a hands-on team in Austin, then outsourcing to Ukraine will almost certainly fail. I was fortunate that our first outsourced hire was able to oversee and communicate with an offshore team. Yet, this isn't always the case.

Ultimately, you'll need to find a way to manage both types of resources effectively.

After wasting tens of thousands of dollars on a dev shop, I was introduced to a technical consultant who had experience working with offshore teams. Our technical consultant helped source and oversee our offshore teams, first in Ukraine and then Pakistan. This saved me a ton of money, as I in many ways had the best of both worlds. I think one of the biggest mistakes founders make early on is trying to go offshore and hire developers when they have never managed offshore developers or, even worse, they aren't themselves technical. It's literally a recipe for disaster. Additionally, if you aren't technical it becomes hard to manage a developer in general. By hiring a technical consultant who worked for me, my offshore team was held accountable because the consultant reported back to me, and not the dev shop.

How can I hire great freelance talent over mediocre ones?

There are several methods that can help you find the right freelancer for your project.

One is to use a curated talent platform. There are plenty out there now, like Toptal and Andela, that have refined processes to offer a reliable, high-quality, and fast method of hiring top freelancers (Toptal only accepts the top 3% of candidates into their talent network). Yet, they can still be very expensive depending on how early you are in starting your business and how many resources you have. At one point we used Andela, but if I'm being frank I believe they had problems maintaining costs as they scaled. Thus, outsourcing through a talent platform with offices in the United States who then outsourced to Africa no longer made sense for us. I thoroughly enjoyed working with our engineer in Kenya who was also a Black woman and was amazing, but it became cost prohibitive and no longer truly made economic sense. From there we outsourced to Pakistan before bringing our entire dev team in house.

What are the pros and cons?

If you're short on time, curated talent platforms can access their network of freelancers, so that you will have just a select few candidates to interview and hire. In many ways they are like a recruiting firm.

Though Toptal offers a no-risk trial period, I am inclined to say that there is no such thing as no risk. Yet, the option allows you to hire a freelancer for your project and pay only if you're completely satisfied with your freelancer's work at the end of the trial period.

The other key item with platforms like this is pricing transparency. For the most part, you know what you get.

Referrals are another way to hire freelancers. If you don't have a trusted network who can recommend freelancers they have worked with or have been referred, then you can begin to build one. There are tons of slack channels and Facebook groups of tech people coming together to share resources and information; seek them out and join them.

What are the pros and cons?

The difficulty of pursuing this method lies in the need to (1) possess your own network of talented freelancers, and (2) attract these freelancers to your project. A great freelancer usually has their pick of projects, which means you may need to offer a higher pay rate or more scheduling flexibility if freelancers are not immediately interested in your project.

Use an agency. If you go this route, you'll have to conduct your due diligence by reading reviews and speaking with each agency, of which there are many. What are the pros/cons? Well, I went the agency route at first and though we were able to get a minimal viable product (MVP) out of it, it's not a long-term solution. It's also going to cost you more than a freelancer because you are hiring a “one-stop shop” to get your product or MVP off the ground. Also note that agencies tend to be less flexible with their working style.

On the plus side, the pricing will be transparent up front for your project needs and the time it will take, though it may shift based on sprints to finish.

Though I've used a combination of these, what I've found is that freelancers recommended by friends or colleagues were almost always the best. What I've also found is that everyone has a different way of doing things. In time. if you hire a CTO or bring on a technical founder they may want to go an entirely different route, which can lead to rebuilding the entire infrastructure of your product if the CTO finds gaps or that engineers took shortcuts for the sake of getting a product to market.

I was pretty particular about staying with the same engineer throughout the duration of the work, and the only instance where this was not the case was when the engineer left the company I was working with. If you are presented with this dilemma, always push back to keep the same engineer working on your project (if the engineer is good).

Key features or QA strategies may be ignored completely, if the contractor falls behind schedule. I have experienced this, and because the agreement or contract made by management was not ironclad, the contractors got away with ditching some activities and features the company wanted.

Additionally, if you aren't a technical founder you are 10 times more likely to get screwed over because you don't know what you don't know. This is another reason why I hired a technical consultant—to ensure that I wasn't making these missteps along the way, which I wouldn't have been able to spot.

Side note: It's extremely difficult for nontechnical founders to raise money, but I believe there are ways to navigate until you find a full-time CTO if you are a solo founder, which is what I did. If you have found a CTO who can be a co-founder, a lot of this won't really apply unless they aren't fully bought in. In that case, you don't really have a co-founder.

Working with contractors may also be difficult because they may take a passive-aggressive posture, which means you need to have someone appointed to do what they said they would do (and agree to work with, transparently, the onshore client development team). You need a manager, or management team, that backs up their offshore team, especially if the goal is to relinquish the further development and maintenance of your product being created offshore.

Some offshore contractors may not want to make it easy to end or let go of the project. It is not in their interest to give that up, and they will probably hold on to control of that project until the customer ends the contract. Also watch out for contractors who may look for excuses to not keep up their end of the agreement (the project is behind schedule, it costs too much, etc.).

Things to improve the situation:

• Have an ironclad agreement in place: I am not an attorney, but it is very important to have everything in writing and signed; this ensures that it's not so easy for the contractor to slide out of things they agreed to do. My technical consultant was really good at helping ensure that everyone remembered what we agreed to do long after we had agreed to it, and continuously as we built. This was also important because I had someone who could create a checks and balances between the company and our developers since I myself am not technical.
• Expect transparency: Make it clear up front that you don't want to just wing it, and that you care about deadlines and quality control as well as transferring knowledge to your onshore in-house development team once that time comes. Schedule daily scrums and meetings with management on a weekly basis (communication will happen). Make it clear that there are consequences to not meeting deadlines, or throwing out QA, functional unit testing, and other agreed-upon items in the contract. Make sure they know the consequences of ignoring these required items. You can also set your contractors to be paid only after a sprint is completed, thus they are financially incentivized to do so.
• Create infrastructure: I believe that the reason we were able to use offshore developers for so long is that we created the infrastructure for them to be able to work within, such as cloud allocation, servers, and so on. Also, ensure they are trained on how to properly deliver completed work. If you work with an offshore team that has a management system in place, they will generally prioritize this as apart of their own built-in infrastructure.
• Always communicate: We communicated often via Slack, but early on our technical consultant also had standing calls/check-ins with our offshore team. Using a daily scrum format every work cycle, day or night (there may be a 15-hour time difference!), may mean that you have to do this at 10 p.m. or 6 or 7 a.m. All the offshore developers will briefly need to tell you (1) what they worked on yesterday (last time cycle), (2) what they plan on working on next, and (3) any impediments that they may have. We had weekly dev calls in which we were able to build rapport with our offshore team. They felt like—and were—an extension of our team, which made them (in my opinion) more accountable for the work they were doing.
• Have a detailed exit strategy: Everyone from my technical consultant to our offshore team knew a day would come when we'd likely transition. We made this clear up front, so that there would be no issues, and if you are working with a credible offshore team there shouldn't be any issues. In our case we brought on a CTO who would be responsible for leading our technical team. Because of this we had no issues with transitioning our offshore team off the work, and having them help with bringing full-time engineers up to speed on the work that we were doing.

I hear offshore horror stories, and I've had a bump in the road or two and understand how this can happen. Founders ask me “What if they just aren't doing what you asked?” I'd say that how a project starts is usually how it will finish, so you'll need to realign quickly and if there is no immediate change, then you should move on. Find another contractor or someone else who can take over the work. If you are close to launching a product or an important feature, then this is where you need to revisit your contract and what you agreed upon. Unfortunately, you'll likely have to just bite the bullet until you can bring another contractor up to speed and transition over.

One of the downsides to temporary offshore teams is that when you do hire full-time dev they will most likely run into problems where the application feels a bit buggy, or some temporary fixes were implemented that, while getting the job done, will need to be fixed for the long term.

At the end of the day, working with offshore teams doesn't have to be a bad experience. It really is all in how the relationship is handled, how the work starts (minus the time difference, it can be just like working with contractors in the United States, as a lot of this information is transferable), and picking the right team. And remember, if it's not working out, pivot quickly if you can.

Out of the Gate

When I first started hiring back during the SGI days I made tons of missteps. I had never hired anyone before and for some reason I never sought out someone to give me advice or coach me along the way early on. Yes, I had read a few management books, but I don't think anything really prepares you for managing people for the first time.

One thing I learned pretty quickly about myself is that I needed to run a hiring process that included the final decision- maker being more than just me and my thoughts about a candidate.

You can sometimes fall so in love with the idea of a candidate that you romanticize not only the position but the person in the position because having the ideal candidate would be a game changer. So you tell yourself that if only you can find this person then you'd be able to do X, Y, Z, and whew wouldn't that be nice.

So, a candidate sits across the table from you and they say all the right things. That's why it's important to run a hiring process that includes having enough people who know what you are looking for to have spoken with the candidate.

Hiring costs you time and money, and when employee turnovers happen early on in their time at the company, it costs you even more.

A candidate doesn't have to have everything on the first day, but they need to show the ability to grow within their role and within the company. Additionally, it's also on you to ensure that they have what they need to do this, within reason. If you are working in a startup then you should expect to work with limited resources; this is why it's so important to find people with grit.

With hires, you are trying to get it right the first time. We wish we could be so lucky that this will always be the case. You just won't get it right every time. Yet, usually within a short period of time you know when it's not right. One thing I've learned is that when you know it's time, let that person go. And if you're anything like me, an empath at heart, then this decision won't be easy. But trust me, it will save you a lot of time, money, and setbacks the quicker you rip the Band-Aid off. And it's probably best for both of you. You don't want someone in a place where they aren't excelling and have to look over their shoulder because they feel the hammer can come down at any moment. Sometimes it's just not a good fit and that's okay. This isn't to say that you shouldn't give promising team members the room to course correct; you should have to have discernment to know the difference.

There are best practices and techniques that will allow you to become a better hiring manager. Not everything has to be a trial-and-error type of experience, as too many mistakes early on can cost you your business.

Recruiting is hard. But it's one of the top jobs you will have as your company grows. So, as our company grew and the positions became more demanding and we had the need to recruit higher-stakes candidates, we moved to hire a recruiter.

A recruiter brings the ability to source much faster through a vetted and sourced network. They work with you to create the right profile and the specifications of the job as well as a detailed background on the company they use to source candidates with.

We also use LinkedIn Recruiter because there have been numerous times that we hired a recruiter to help source for us, but then someone within our network, even one of our own team members, referred someone we ultimately hired.

Yet, I still believe in hiring external recruiters when you can afford to, especially as you scale and it becomes critical that you source rock star candidates in key roles. You do still have to be very active in the process even though you have a recruiter on board. This means responding promptly to requests and getting candidates scheduled. Usually recruiters charge either anywhere between 10% and 20% of the candidate's first-year salary or a base price.

There are two different types of recruiters: contingency or retained.

We've used both.

Contingency versus Retained Recruiters

There are two types of contingency searches and generally two types of retained searches as well. There are contingency recruiters that are exclusive, meaning that the assignment has been given to a sole agency and won't involve payment until a candidate is actually placed. Then there are nonexclusive contingency recruiters, which means you are shopping around and likely have other recruiting agencies doing the search as well. There is also no payment involved until the candidate is placed.

There are also two types of retained recruitment agencies. There is the standard retained recruiter, which usually involves two payments: a standard fee to engage and another payment once the candidate is found. Then there is the engagement fee retained recruiter. This one you should be mindful of because the agency receives a portion of the fee up front and it's not refundable if you were to stop the search or find a candidate via a means other than the agency.

We've used both types of agencies and have paid upwards of $25,000 to secure a VP or higher in retained recruitment agencies. We found our C-suite recruiter via a recommendation. He had just left a larger firm where he had placed hundreds of people, and was venturing off to start his own agency. We were able to get him for half the usual price because of this, but he came with all the knowledge, tools, and resources to effectively recruit like a top-tier agency. For team members at the management or director level, this number was considerably lower. Yet, the numbers fluctuate significantly depending on the company you use, and their track record.

Another consideration, once you can afford it, is bringing your recruiter in-house. Matt Roberge, author of The Sales Automation Formula (Wiley, 2015), is a fan of this method. Instead of hiring a recruiter, he made an offer to bring the recruiter in-house, promising that the company would be much more successful this way. At Resilia, we'll hire our first Director of People Ops in 2021, who will also be responsible for managing, hiring, and further building out our culture at the company.

If you do not have the ability to hire a recruiter, turn LinkedIn into your personal recruiter, free of charge.

It's one of the most powerful tools I've found for hiring because you can use the search engine to source candidates by their current position, company, and other relevant facts.

Say you are looking for a salesperson. You can search companies that might align to yours, and give someone in a later-stage company than yours an opportunity to use the skills they gained to help a company that's earlier stage and have the opportunity for upside that might be unattainable in their current role. You can also see relevant activity of the candidate and glean some insights on whether you want to reach out and engage. If you do, then you can contact them via LinkedIn.

Because of COVID-19, the talent pool got much wider due to layoffs across the tech sector and in nearly every industry. The general rule of thumb that the best candidates aren't looking for job opportunities isn't necessarily true now, because candidates were getting let go not because of performance but because of steep cuts. I have a friend who had just left a great job he had been in for the past five years for an opportunity at a very-well-known tech company in January of 2020, and within just three months at his new job he, along with the majority of his HR department, lost his job.

Yet, regardless of the times you're still looking at high-performing individuals who are potentially looking for a challenge, a new opportunity to work with a start-up and one driven by a mission that they can be proud to say they are a part of.

At some point, particularly with millennials, people want to work at a company that is striving to have a greater impact and to create lasting human connections. Thus, our mission has helped us recruit talent from other companies and because of this our ratio of closing candidates is very high.

Once you've made the hire, now you have to take a candidate through onboarding.

It is said that a candidate knows within the first weeks or months whether they want to stay at a company. This is in large part due to their onboarding experience. We have spent time crafting our onboarding experience and, since we are an early startup, continue to iterate on this process. We also ask our new hires to give feedback on their experience, as it's important for us to build a culture where people feel that they can speak up.

The onboarding process is about integrating a new employee into our company and our culture as well as ensuring that the new hire has the tools and key information needed to thrive in their role. Yes, it includes things like getting a computer and joining Asana, Slack, and other systems of record, but it also means doing deep dives with team members across the company.

As soon as a new hire receives an offer letter and accepts, we begin to onboard them via an online portal with Justworks. If you aren't familiar with Justworks, it's a platform that helps employers manage payroll, benefits, employee information, and employment-related compliance. Here they can immediately discover information designed to engage them around the company.

As I mentioned, my very first full-time hire ever was in 2010, which means I've now been consistently hiring full-time people for over 10 years. My first hire wasn't an assistant, although sometimes I feel that people default to hiring an assistant as their first hire, and this might be an extreme need for many. For me, hiring someone I referred to as a generalist, someone who could wear multiple hats and was a logistics dream, was my first hire. I also broke one of my rules: let your friends stay your friends; don't hire them unless they are superb and bring proven skills to the table in a needed role. My first hire was one of my best friends, Shayla. Yet, I had worked with her through my sorority in college, I had lived with her as roommates, I had depended on her as a friend. So, when it came time to start my company she was the first person I thought about. She was in with no hesitation. At this time, we were both in grad school but we took the challenge full on.

We'd go on to grow Solid Ground pretty significantly in a short period of time. Not bad for two first-generation college students who had always been self-starters. After several years, she'd move on, going back to school to become a social worker and a photographer, proving that where you start doesn't always have to be your long-term trajectory. I cheered her on, as I do any of my team members who depart the company. It is without a doubt that I want those around me to do work they love and to live out their life as they imagine it.

While I was writing this book, I received a text from Shayla out of the blue. It said, “I've been wanting to say it for a while—thank you for all the opportunities that you have sent my way over the years. I hope you are well, my friend.”

Managing teams, hiring, firing—none of it really gets easier but you do get better at it. If you want to run a successful company, you must get better at it.

Get Out of the Way

Now that you've hired these competent, capable people to help run parts of your company, it's time to get out of the way.

You really need to rely on your team to take on the work that you've hired them to do. As your company grows, you just don't have time for it.

You also have to learn to rely on them to make decisions in an early-stage startup.

Early on, you'll likely be the person with the most context on the business and as a result, you'll tend to be involved in almost all decisions, but when you're larger, you can no longer know everything about everything.

You need to shift from always being in the know about every single detail to enabling others to make decisions. I'll admit that this was an interesting adjustment for me in the early days. I knew virtually everything that was happening across the business at Solid Ground and when I started Resilia.

Yet, once you have so much going on at such high velocity that no one person can really stay on top of it all, especially as you are now hiring key leaders who are experts in their space, you aren't always in the best place to recommend the best course of action on certain topics for the business. So what do you do to teach yourself to delegate not only work but decision-making to the people you are hiring?

As the founder, you probably still have the best information and perspective on the company, and, yes, it is still important to connect all the dots. So, your role is to have context across the various parts of the company, which is an important role of the CEO, but you have to effectively push that context down to others, so that they can make informed decisions that are right for the company.

Once we started hiring senior leadership I really tried to hone in on this, but starting it even earlier can avoid a bottleneck, severely limiting your company's ability, as you continue to grow.

At the onset of COVID-19 things were evolving very quickly on a national and global scale and, like most companies, we had to make a series of critical decisions for our business and our employees. We have two offices; one we had just opened in January of 2020. Today, our team is still working remotely, though we don't suspect it will be permanent. The role of each managing team member is more important than ever now. They are responsible for those who report up to them and they also have to understand how their team feels, what's causing issues for them within (or outside) of the company, and how to resolve problems where feasible.

Managers are usually empowered by someone on the senior leadership team who is communicating their vision and expectations and working to keep things on course. Yet, their role isn't to micromanage.

This is why it's important to empower your team to make decisions, build a culture of trust, and explicitly let members on your team make decisions on behalf of the company. Create clear expectations so they know which decisions should be elevated to leadership for approval, and facilitate cross-functional collaboration to avoid dysfunctional silos where all decisions that span two or more functions get elevated to you; instead, I try to ensure that folks have the right information to make these decisions. You can continue on other work and focus on thoughtful communication to make sure that everybody's on the same page. That brings me to our next topic: the way you communicate changes a lot as you scale.

Earlier-stage relationships are close enough that it's easier at this stage, but this changes as your company grows; people have different perspectives from their individual experiences in areas of the business. They have different priorities, and they digest and understand information in dramatically different ways. Someone once told me that if you want folks to remember something you have to tell them five times in five different ways. I think that's a great way to think about it in a larger company; communication may not be as straightforward. The principles of communication remain the same as you grow. You have to be thoughtful about what and when you communicate and the implications of those decisions. Everyone likes to talk about transparency; transparency is important, but one of the things that folks talk about less is the timing of that transparency and how communications are rolled out. I don't like to spring anything that's a surprise on my team without a well-thought-out plan and the objective of the follow-on message. My CTO definitely holds my feet to the fire on this one. I'll run something by him and he'll suggest perhaps a different tone. If you know my personality then you know I'm a straight shooter, and I often don't mince words. Most of you might say, “well, that sounds right to me!” But as your team grows, if you want to retain talent you have to constantly check your tone and ensure that your approach isn't abrasive in a way that's offensive.

Transparency changes as you scale and grow because you have to be more thoughtful about how information cascades throughout your organization.

This helps equip your senior leadership to respond appropriately themselves and be prepared to answer any questions that come up if managers have questions or concerns.

It gives you time to make sure they're well informed and bought into whatever you're rolling out. I think effective transparency has four key characteristics:

• First, your communication should be timely. You might have the right message, but if your timing is off and you share important information with your team too late, you can come across as reactive on the flip side. If you talk about something too early, you can cause a huge amount of disruption, uncertainty, and speculation in your organization that distracts the team from keeping the business moving forward.
• Second, your communication should be strategic; always focus on why you're making this change, how it supports your strategy, how it will help you and your team achieve your mission, and strategize to build buy-in over time rather than expecting immediate adoption.

  Something we are trying to work on is when we have a series of updates coming out across multiple channels, to help people and keep them posted in advance of the changes being rolled out. Expressing clear instructions on where to go with questions is important.

  Third, your communication should be shareable. What I mean by this is that the messaging should be clear and easy to follow without room for misinterpretation or guesswork. It should also be as concise as possible. As your team grows, consider communicating using different channels. I mentioned earlier to leverage your management structure to cascade information. For us, this means making use of our internal content-sharing platform as well as Slack and highlighting important messages and weekly news updates, as well as covering them in our All Hands, which consists of everyone on our team. We make room for discussion in all of our All Hands and embed a Q&A document just in case someone doesn't feel comfortable asking a question in front of the entire team, but wants the question addressed during the team meeting as there might be others with the same question.

• Finally, your communication should be actionable. If you're expecting your team to react in a certain way or with a specific set of actions, make sure that it's abundantly clear if there's a way for them to contribute and ways they can do so.

  Let your team know how the information you share with them will impact them, what questions you have of them, and how they can contribute. This could mean keeping an eye out for further information, setting aside a time on their calendars for training, or providing feedback on an important topic.