My Most Valuable Leadership Lesson Came From My Greatest Hiring Failure

One of the most confusing and confounding bad hires I ever made taught me my most important hiring AND leadership lesson.

I was a few months into my first executive role at a Startup here in Austin, and ensuring that we hired quality, talented Software Engineers was ultimately my responsibility. 

We’d just hired a mid-level software engineer who’d come over from a much larger tech company, and while they were clearly bright and technically capable, after a few weeks it seemed like this hire might not have been a good decision. 

This person was rushing through their work, sacrificing quality in their code, not testing it, not having anyone else review it … all red flags in our organization and the standards by which we did things.

I talked with the Engineer’s manager, who met with her to discuss our concerns, and he came back to me pretty perplexed. He had the conversation, and this Engineer of his was insistent they were doing really well because they’d “done a lot of tickets”, and they were actually offended we’d claim otherwise. I chatted with the Manager, and we came up with a plan to try and better communicate that we weren’t all about silo-ing yourself off, putting your head down and cranking out a ton of tasks with no concern for quality and no collaboration with or input from teammates.

Despite our best efforts, we couldn’t get on the same page, they continued to protest our performance concerns and maintained they were doing great work because of the number of tickets they had gone through. Eventually we decided to part ways with this Engineer, and it really left me scratching my head.

To this day, any firing decision takes a lot out of me, even when I know it’s the right call and it pretty much always ends up being the best decision for both the company and the employee. 

And, in the case of a bad hire, we had developed the really useful habit of doing a “post-mortem” or retrospective on where we went wrong, and could this bad hire have been avoided? Most of the time, we learned at least one or two good lessons which allowed us to avoid making the same mistake twice.

With this one, though, I was really confused. I kept trying to figure out what went wrong? 

We’d gone through our normal screening & interview process, which was rigorous but pretty reliable AND fair to candidates. This person had even attended a department happy hour event and met a number of people on our teams, all of whom agreed they were smart, humble, eager to learn and grow, and basically every other trait we valued in team members.

So how were we so misaligned with this person on expectations? In a lot of ways, I felt like I’d failed them. Were we not clear about our style of working, collaboratively, with a commitment to quality over raw, breakneck speed? Why were they so insistent they were performing really well, even as we repeatedly explained that cranking out a bunch of tickets wasn’t our definition of success?

Then a thought struck me. We always talk about what people do on a day-to-day basis. The knowledge & expertise we need, the programming languages they needed to know, the tools we use. 

And we talk about that stuff all over the place. Job Ads, Internal Job Descriptions, Social Media posts, in conversations during Screens & Interviews. We talk until we’re blue in the face about what they would be doing, but we never talk about what would make them successful.

I thought maybe I was onto something, but I wanted to be sure. So I started casually asking around, in conversation with the other people in my department. And the more people I asked, the more I started to realize that it was hard-to-impossible for a LOT of people in my department team to clearly articulate what success looked like in their given position. 

I suddenly realized that, even as an Executive, as Director, I couldn’t really describe let alone define success for my position, either. 

So, out of curiosity, I asked my boss (our CTO), and here to find out he couldn’t really do it for his position either.

Mind you, I’m not talking about precise metrics or quantifiable goals here, just the basic parameters for success.

And that’s when I realized it doesn’t matter whether somebody has all of the qualifications, years of experience, and skills you’re looking for. It doesn’t matter if they’re a “technical” fit AND a “culture” fit. As an executive, as a hiring manager, as a company leader, it’s up to me to get as clear as I can about how someone will be successful in a given role, and to be able to communicate that clearly and concisely in all my recruiting efforts as well as with current employees.

Without clearly understanding and communicating how someone can be successful, I am setting us all up for failure.

Unfortunately this realization came all too late for that particular Engineer and for that organization, and yet it now serves as the starting point for how I build & grow teams, and in what I teach to other decision-makers tasked with hiring responsibilities: How someone is successful in a given position is all in how they deliver value to customers, the company, their colleagues, and themselves.

When you think about any position starting from the place of how they add value, everything else becomes easier.

So maybe set aside some time — even as little as just 5 minutes — grab a sheet of paper, and ask yourself “How would I know if I’m successful in my current position?” If you’re a Hiring Manager, see if you can clearly articulate success for the positions you manage as well as the positions you’re trying to fill, now and in the future.

Learn from my mistake and you’ll save everyone a ton of time, money, and frustration.

The “Culture Fit” Fix

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Read the blog below, stream the podcast version, or watch the video here!

Is your unspoken definition of “culture fit” actually hurting your organization?

Is it possible that your current approach in assessing a candidate’s ability to fit in your organization is actually hindering your growth and preventing your success? Can you clearly speak to what it exactly means to be a ‘culture fit’ in your environment? 

Continue reading “The “Culture Fit” Fix”

Talent Scouts-as-a-Service?

I spend a lot of time thinking about the Hiring space, specifically as it relates to the problems & challenges faced by smaller employers.

One of my favorite “Thinking Time” questions is

“What are the gaps between my customers’ needs and the products & services that are available?”

(for more on Thinking Time, see the must-read book The Road Less Stupid by Keith Cunningham)

Here are some of the key problems I observe in companies that are beyond that “scrappy bootstrapped” phase but without multiple consecutive years of impressive, steady growth.

  1. Sourcing good candidates is a huge issue, if not THE primary roadblock
  2. CoFounders, Executives, Hiring Managers are still primarily in DOING mode vs LEADING mode
  3. Recruiters, whether FT On-Staff or Contracted by a service, spend a lot of their time operating & coordinating. Sometimes your “Recruiter” is an HR Generalist-type, who doesn’t have that recruiting background
  4. These companies by-and-large balk at Agency Recruiter Fees
  5. Almost every single one of these companies spends their time reacting to sudden hiring needs and open roles… which introduces additional chaos and churn… which extends time-to-hire among other things

Here are Early stages of an idea to fill these gaps. I’m not implementing this idea, mind you, simply brainstorming.

In sports (and other industries), organizations have talent scouts whose primary responsibility is to identify, evaluate and start building relationships with players the team may be interested in, whether now OR in the short-to-medium term future. The relationships they build keep the players as “warm leads” so the team can stay prepared and doesn’t get caught with its pants down needing to fill a particular position all of a sudden.

(It’s also worth noting that many large corporations dedicate full-time employees to the purpose of scouting.)

What I’m picturing is this provided as a subscription service targeted at smaller, time- and resource-constrained organizations.

The “Talent Scout” spends a little time with company leadership on a recurring basis to identify positions and skillsets they may need in the near future. They then connect the talent they meet with the company, but on a casual, low-pressure basis (this is the other problem for in-demand talent: Recruiters & Headhunters *can* be pushy & relentless, a huge turnoff). The Talent gets to know the Company, and if turnover or growth leads to an open spot, it could be filled rather quickly by someone on this bench.

For argument’s sake, let’s say Monthly Cost to the Employer is around $5–10k (could tier it based on number & type of positions or something), lower than almost any 15–25% Recruiter Fees on a single hire. Risk to the Employer is paying for months when they have zero need for hiring (which, given high average turnover rates, seems fairly low risk)

Benefits include the ability to better anticipate future staffing needs, reducing reactive behavior, shortening time-to-hire, less time & energy spent sourcing (and most likely for less $$ than an Agency).

Admittedly, there are bound to be a hundred holes in this idea, as I haven’t vetted it beyond the concept stage. I also haven’t researched a ton of comps, so maybe it’s the least original idea ever.

But for those of you in small-to-medium businesses, especially those on a Hiring Team, I’m curious to hear your thoughts.

Drop me a comment and let me know: Does any of this sound like it would be valuable, time-saving, effort-saving in your organization?

5 Ways to Dramatically Upgrade Candidate Outreach

As a business leader, it’s probably obvious that the Field of Dreams adage “If you build it, they will come”, while one of the most recognizable movie lines of all time, is very much a dream. Having a valuable product or service is not enough without a way to get it in front of the people who would be interested in the value it provides.

The same holds true for the opportunities you offer as an employer. You could have the most outstanding company culture, offer unparalleled benefits or pay 3x the salary of your competition, but if the people who you want to hire don’t know about the role, the results you see in terms of engaged applicants are going to be underwhelming at best.

Sourcing great talent is one component in what I call the 5 Components of High Performance Hiring, and it’s one to which most Employers dedicate insufficient attention & resources.

Download your FREE 5 Components of High Performance Hiring Cheatsheet

No matter the job market conditions, direct outreach is a critical Sourcing sub-component. If you want to hire people who are bright, hungry self-starters, and can make an impact early on, you’re going to be looking for people who are already gainfully employed and either passive job-seekers or not even thinking about new opportunities.

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Implementing the following 5 Practices will dramatically upgrade the engagement you’ll see when you reach out directly to A+ Talent.
(Note: These practices & strategies are excerpts from my new book Hack Your Hiring: The Tactical Playbook to Find, Evaluate, and Hire A+ Talent, available now on Amazon.)

#1: Target Candidates Who Know a Colleague

When sourcing leads for recruiting outreach, target candidates who are connected on Facebook/LinkedIn/etc. to a current member of your staff.

In HIRED’s 2018 Employer Brand Survey, 45% of candidates said a primary reason they’ll engage with a company is if a friend or former colleague works there6t. So whether your colleagues put in the effort to provide referrals or not, it should not deter you from focusing your efforts on people they know and/or have worked with previously.

#2: Send Prospects a Free Gift

Empower Recruiters, Recruiting Researchers, & Recruiting Coordinators to send something of value to passive talent to get her engaged in the recruiting process. It can be something as simple as a link to an interesting article, video or product related to her discipline or area of expertise.

A-Players are already gun-shy when it comes to recruiting outreach, and it’s not surprising as to why. Most Managers and Recruiters initiate outreach the complete wrong way: By focusing on themselves. This “Look at me and my great opportunity” approach is a big turn-off to an uber-talented person who gets hassled about new opportunities on a weekly or even daily basis.

The gift you send does not need to be expensive or even have any material cost, as long as it provides value.

In addition to breaking the pattern of bad behavior and thus immediately getting her attention, you may trigger a concept known as The Reciprocity Principle. The Reciprocity Principle is a well-documented principle of persuasion. Simply put, people are obliged to give back to others when they receive a gift or service first to ensure the interaction is balanced.

#3: Send a Personalized Message

When initiating Outbound contact with a Prospect, reference specific details about her work history, current role or interests. Ask a targeted question about one of these areas that will entice her to reply.

Recruiters & Hiring Managers have a tendency to play the numbers game when it comes to candidate outreach, relying on templates and form letters for the bulk of their communication. In a candidate-driven market, the key to grabbing an A-Player’s attention is to make her feel special, like she’s not just another number. If you can convey to her that you did your homework and that you want to learn more about her unique experiences & interests, she’s far more likely to engage.

#4: Focus on HER Interests, Not Yours

When Sourcing passive candidates, spend the majority of the time asking about their current challenges and career goals, and then genuinely listening to their responses.

Everyone loves talking about their favorite subject: Themselves.

By asking simple, targeted questions about a job-seeker’s current & desired career conditions, you get them to open up and connect with you. Now that you’ve established a genuine connection, she’s more likely to become and stay engaged in your recruiting process.

NOTE: This is a great strategy for outbound sourcing, when candidates haven’t yet indicated interest in your or your opportunity. It can, however, also be useful with those who have already applied for the role.

#5: Share Salary Up Front

Whether it’s posted with your position description on job boards, or you keep it handy when having initial conversations with potential candidates, be transparent in letting them know what the salary range is for the role, as well as additional benefits the company offers (both material & intangible).

Compensation is consistently rated as one the top 3 reasons people decide to look for new opportunities. HIRED reports that 62% of candidates said a primary reason they’ll engage with a company is when they get the salary range up-front.

By sharing compensation details (salary, benefits, perks) early in the process, job-seekers will be able to decide if the salary range is aligned with their expectations.
Employers who go out of their way to obscure salary set themselves up for failure from the start, as they waste time evaluating candidates they can’t afford. And since platforms like Glassdoor allow current & former employees to submit their salary information that will then be shared publicly, why try to hide it?


I know from years of experience how frustrating it can be trying to fill open positions with awesome, talented people. My years as an executive — constantly dealing with the needs of a growing business and backfilling outgoing team members — served as an outstanding education.

Hopefully you’ll start to implement practices like the ones above and create real transformation in your hiring efforts. These practices are literally just the tip of the spear. You’ll get over 15x additional value when you pick up your copy of Hack Your Hiring on Amazon. Until then, Happy Hunting and Happy Hiring!

How to Fix the Top of Your Recruiting Funnel

In this post, I’d like to share tips on how to improve the top of your candidate funnel. Whether you don’t have anybody applying for your job, or it’s just not the right people, I want to provide the tips and tools that you can use to improve the top of the recruiting funnel.

So the first thing you’re gonna wanna do is get crystal clear on who exactly it is that you’re targeting here. Now, I know that you think you might have already done that by writing up a job description / job ad and posting it out online. But what I’m talking about is a little bit different. I want you to really think about who it is that you want applying for this job opening that you have.

What job are they currently in? Why would they be considering looking for a new job? Are they just unsatisfied with where they’re at right now? Are they looking for new opportunities? Are they looking for new challenges? Are they just looking for a change?

So, get crystal clear on what would drive them to be looking for a new opportunity. What do they want in a new job? What do they really need? Where are they spending their time, online and offline? By getting clear on this avatar of who it is that you want applying for your job, you start to get some better ideas about how you might actually reach them. Then I want you to look at your job description. Is the way that you’ve laid it out focused solely on what you need from this person, or is there anything in there about how you might satisfy some of the things that they desire, that they’re looking for in a new opportunity?

You’re also gonna want to really take another look in how you present your organization to candidates. Just like every job description is usually a boring, bullet point list of skills and responsibilities, most company descriptions are yawn-inducing history lessons about how the company was founded, when it was founded, how long you’ve been in business, and how big your team is. These sorts of things aren’t going to appeal to most people, but it is what we naturally go with.

So, now that you know who your candidate is, and what it is they want in an opportunity, what do you think they might want in an organization? What strengths that you have in your organization can you communicate to them? How would you describe your team? Your company culture? Does your company celebrate or embody principles and values that could be attractive to any candidate, especially the one you really, really wanna hire? Is there a way that you can uniquely communicate this to people, before they even consider applying?

You know, there’s a saying that “people don’t leave jobs, they leave managers.” And I firmly believe that that is true. That said, it’s also true that people don’t join a company for a paycheck or a list of responsibilities. They join a company because of the people, the leadership, the folks that they meet during the interview process. So, are you truly presenting your leadership — yourself, from the CEO all the way down to the people that your ideal hire’s gonna be working with — are you presenting them to the candidate in any way, shape, or form, before they actually come in for an interview? Introducing a human element into how you present your organization, your leadership, your team, can really go a long way in convincing your ideal candidate to apply and engage in the recruiting process.

Okay, so now you’ve got all this nailed down, you have your ideal candidate avatar. You really understand what they want in an opportunity, and what they’re looking for in an organization, and you’re able to communicate that to them. Now you’re going to want to present all of this using persuasive language. And you might need to hire a copywriter, or use your marketing team, or something, whenever you’re doing this. It will go such a long way in improving the top of your funnel.

Because most job ads are cold and corporate. And as I mentioned, people don’t leave jobs, they leave managers. They also don’t join job descriptions, they join teams of people. So these cold, corporate, formulaic job ads are just really not doing anybody any favors.

So, gather your notes. Go to somebody you trust as a good writer, or a great marketer, and get them to whip something up for you. I think you’ll be presently surprised, even by the first draft, and then you can iterate from there. It doesn’t have to be perfect the first time out, but I can almost guarantee it’s gonna be better than what you’re putting out there right now.

I wanted to keep this brief, and I hope it was helpful for you. I guarantee if you put some of these things into practice, the number and the quality of people that are applying for your role is going to improve exponentially. If you’ve enjoyed this post, please like/clap/share it all over the Interwebz.

Lessons From HIRED on Candidate Outreach

The first week of October came and went, recently, and with it Austin Startup Week 2018. In years past, I was so hyper-focused on the responsibilities as an employee in the Austin startup scene that I rarely took advantage of the hundreds of panels, speakers and events that were available.

This year, being self-employed afforded the opportunity to grant myself permission to fully participate. In addition to (hopefully) providing value in my own talk — Engineering Excellence: Best Practices of High-Performing Teams — I got to spend at least a little time attending a handful of sessions.

One of the sessions in the HR and Culture track was especially attractive, given a focus & obsession I have to help growing companies attract, acquire & retain the type of talent they need to grow and succeed. It was a panel discussion titled Your Employer Brand: Strategies that Attract Top Tech Talent, hosted at Walmart Tech and sponsored by HIRED.

The supplemental materials provided by the sponsor included their 2018 Global Brand Health Report, a 51-page booklet where “Tech workers reveal the companies they want to work for and what they value in a job offer.”

The Report, while brief, provided a ton of useful data and insights. What follows are just a few takeaways that could be valuable for any employer, regardless of size or industry.

Prologue: We’re [ALL] Hiring

It’s safe to say that nearly every organization has one or more open positions at the moment. If your company is growing, you’re hiring. If your growth has leveled-off, you’ve probably lost a couple team members to new opportunities, so you’re trying to backfill those positions. If you’re in the uncomfortable position of being a business on the decline, you could very well have the most urgent hiring needs out of anyone.

At last measurement in September, unemployment in the U.S. was reported at around 3.7%. Rather than get into how unemployment rates, inflation, wage hikes and other factors all impact one another, it’s best to understand that 3.7% unemployment is the lowest rate in nearly 50 years.

Point is: The Job Market is TIGHT, which means you as an employer need to at least consider anything that can provide a competitive advantage. While I knew some of these things at the time, I wish I’d had all of this information when I was fighting the good fight as a hiring manager.

Insights for Successful Outreach (AKA “Outbound Sales for HR”)

Due to these “Full Employment” conditions, any company who is aggressively staffing-up must be reaching out to job-seekers in a variety of ways if they hope to be successful. So what contributes to successful outreach? Some of the things that make candidates most likely to engage with your company include when:

  1. You disclose Salary information up-front
    More and more employers provide some level of transparent compensation data to their employees, so why not extend that information to job-seekers? There are dozens of websites reporting industry averages and even reported salaries from your company’s current and former employees across a variety of positions. A lot of times, that data is outdated or even simply inaccurate. You might as well set the record straight with potential candidates. At best, they find the transparency refreshing and the salary range attractive enough to engage. At worst, you lose the interest of someone who would eventually turn down your opportunity on the basis of salary, and you’ve just saved a bunch of people hours of their time.

    RECOMMENDATION:
     Reach out prepared with the full package of compensation and benefits, so the talent you’re so interested in has a fullunderstanding of what you offer.

  2. You clearly communicate work experience expectations
    There’s a reason the term “Passive job-seekers” exists: They’re not engaged in the time- and focus-commitment that’s required of actively considering new opportunities. So when they are attracted to a new opportunity, they want to be as confident as possible that they’re a fit on paper. Does “5–7 years Java experience” really mean 5–7 years, or is it negotiable if they have some other valuable and hard-to-find expertise?

    RECOMMENDATIONS:
     Before contacting talent, get crystal clear with hiring managers on what skills (and skill-levels) are completely non-negotiable, and where there might be some wiggle room. Also, work with hiring managers to better describe the degree of expertise they want for each skill. If you’ve ever met someone with 10 years experience who reallyhad the same 1 year of experience for 10 straight years, you’ll know what I mean.
  3. They receive a personalized message
    I’ll keep saying this to anyone who’ll listen: Recruiting and Dating are basically the same thing (Seriously, the parallels are astounding and a little bit depressing). And, as it is in Dating, nobody wants to feel like another faceless name — or is it nameless face? — in some soulless numbers game. They want to feel special, like they’re the prettiest girl at this dance. The least you can do is communicate with them like they’re a human being.

    RECOMMENDATION:
     Do your research. At minimum, find out one or two remotely interesting things, even if it’s just about their alma mater, the length of tenure, or the series of promotions they received at their current gig. Ask them a question outside of whether they’re “currently considering new opportunities.”
  4. They recognize the company name
    In another post, I’ll outline a few turn-offs that revolve around company product & mission. For now, though, it’s a pretty low bar for a candidate to say, “I’ll talk to you if I’ve heard OF the company.”

    RECOMMENDATION: Increase company visibility in the local community and on social media. Sponsor industry and community events. For a few hundred dollars you could overcome the most basic of hurdles that could keep a job-seeker from engaging with you.

  5. They know a friend or former colleague who works at your company
    That we live in the most connected time in history should surprise no one. And in a tight job economy, the best talent is only going to leave the comfort and security of their current job if they greatly minimize their own risk. Part of the research they do on a new suitor (that’s you) is going to include tapping their network for the inside scoop on your organization.
    RECOMMENDATION: Focus the bulk of your efforts on talent who has some kind of connection to your company, even if they’re 2 or 3 degrees from Kevin Bacon himself.

In summary, there are a lot of wrong ways to operate as an employer, staffing firm or recruiting agency when it comes to candidate outreach. Perhaps, if you can focus first on doing the things that talent likes, you won’t have to rely so much on the cringe-inducing tactics that make candidates want to avoid “playing the field” for the rest of time.