Sick of always being on the nervous end of the negotiation table? Well, let's take an exercise today, just for fun, and take on the role of a hiring manager at a medium-sized company. I'll start by presenting the scenario, and then take a look at three candidates, at which point you will select one candidate (and you can provide reasoning for why you picked who in the comments).

Before we get started, a few disclaimers. One, all of the characters, companies, etc. are completely hypothetical and came straight from my ever-wandering mind. And secondly, I will make some assumptions that aren't always true, based on the experience, background, and record of each candidate. Realistically, if we were down to only three candidates, interviews and skills tests would be the determining factors most likely. But it's just hypothetical, right? Just for fun, and to see things from another perspective.

The Company
You work at Centaur Shipping, a logistics company with about 100 employees. Your company serves medium to large organizations by providing tracking software that helps organizations manage their warehouse supply, freight trucks, etc. to be more efficient in their shipping business. Your company's core strength is its cutting-edge software programs, and a staff that is well-versed in this technology and can translate it into clear business efficiencies.

In addition to account managers, marketing people, administrative staff, accountants, and other roles, you have several IT professionals in your organization. You are the IT manager, overseeing your small crew. You currently have one employee who oversees email/Exchange, manages the staff's BlackBerry devices, and handles some other assorted tasks. Another employee handles SharePoint, Active Directory, and troubleshoots as problems arrive.

The open position, the final cog in your wheel, is for a do-it-all generalist that can become well-versed in the tracking software and troubleshoot errors. This employee will also have an important role with new software deployments. He or she will also be expected to serve a strategic role in determining limitations of the company's hardware and software, and report these concerns directly to you, the IT manager. All in all, this person has the closest pulse on employee needs of your IT staff.

What You Want
Before even opening up the position, you've begun to craft the type of worker you want. You want someone who is independent, and can quickly become acclimated with the new system and how Centaur does business. You want someone who is smart and fast, and can make important decisions on the fly without fear or error. Lastly, you want someone who is loyal and committed to making the company the strongest it can be.

Your boss, the director of business development, has left you with a fairly open budget for the employee—$35-60k salary. If you could get a competent employee in the lower echelon, that'd certainly earn you kudos, but the position is important enough that your priority, by far, is finding the right candidate.

The last concern is that you have a number of newer employees who have little technology experience, especially some of your account managers (sales staff). These are people people, and interpersonal relationships are important to them. You need someone who can explain complex concepts to them and also build healthy relationships to maintain morale. The previous employee to hold this role was a guy named Oscar, who was smart, funny, and well liked. However, his technical expertise lacked, so you had to let him go.

After the jump, we'll take a look at our candidates.

Candidate 1: Trevor
Trevor is a young, talented, new college graduate. He's friendly, respectful, and very eager to impress a new boss and grow internally with a good company. While his relative inexperience is a concern, he shows promise based on his success at the reputable college he attended, as well as glowing remarks from an internship he held his senior year.

Opportunities: As a fresh face, Trevor would be eager to please, quickly adapting to the needs of both the organization and the staff. He would be well-liked, as Oscar (the person who held the position before) was. You believe he'd be able to quickly pick up your organization's software and would put significant effort into his work. You also believe he would be a loyal employee, provided he received adequate pay and recognition. And speaking of pay, you surmise you'd be able to get him for the lower end of the salary spectrum.

Concerns: Given that your previous employee in this role was a young, fun guy, you're afraid that the honchos might question your judgment in selecting a similar candidate to last time. (Though, you do see Trevor as different from Oscar, and think you could make him fit.) Another key concern is that given his inexperience, Trevor wouldn't bring the wealth of background experience that some more seasoned candidates do to a new organization, providing a valuable assessment of the organization's strengths and weaknesses before getting too versed in the company structure. You also worry that he might be hesitant to point out problems and concerns, and be slow to assume new software or hardware is needed to make the company flow.

Candidate 2: Greg
Greg is an administrator with good experience and tons of promise. He's been in the industry for eight years, and has earned a glowing reputations as a problem solver, go-getter, above-and-beyond A player. In his relatively short time of experience, he has excelled up the company ladder several times, jumping from a small marketing company to a significant administrator role at a major technology company. Unfortunately, you fear that motivating Greg and keeping him happy will be a concern, and you also sense that he has an inflated ego and might try to take charge of the reins if you hire him.

Opportunities: With Greg's experience, wit, and top-notch training, bringing him into your organization would be like bringing a valued consultant to work full time. You can just imagine the handful of valuable ideas he'll bring to the table. You have little doubt that if Greg joins the team, he'll shake things up, but in a good way. He'll enhance efficiencies and, if Centaur is able to adequately motivate him with perks and bonuses, he might eventually take on a high-level management position in the organization. (Your boss has been nudging you for awhile that you need to work on hiring tomorrow's leaders.)

Concerns: Despite Greg's startling credentials, you fear that his personality might clash with the organization. Centaur is made up largely of A-type account executives, big personalities with a specific idea of how things should be done. You sense some major potential character clashes with employees that are struggling with the technology and this new, likely unforgiving systems admin. The more a person expects from himself, the more he expects from others, you figure. Also, Greg will likely be a ruthless negotiator on salary, pushing you to your limit or beyond, and he'll require bonuses and perks to stay motivated.

Candidate 3: Jane
Jane is a competent, seasoned professional, with 20+ years experience serving a variety of administrator functions. She has experience with large-scale organizational deployments and has dealt with employees of all types and personalities. She has a likeable personality but also a strong knowledge of technology, business, and people. She was laid off from the organization that she worked at for 15 years when the corporation hit tough times and cut 10 percent of its staff.

Opportunities: Jane offers a lot to Centaur—loyalty, competence, and personality. You have little doubt that she'll click with your account managers, and also take the time to help those struggling with the technology. However, she can also hold her own when faced with company crises or major deployments. You want someone that will really commit to Centaur, and you believe Jane is such a candidate.

Concerns: As an organization that focuses on cutting-edge technology , you worry that Jane might struggle with the new systems and might tire of the constant change that is common in Centaur. Your company has a way of doing things differently, and getting deeply immersed in the company culture is important. Also, as a hiring manager 10 years her junior, you worry that she might have some animosity in taking direct orders on technical decisions from you, especially since your background is as much business strategy as it is IT.

On page three, we'll discuss final thoughts, and you'll have the chance to cast your vote.

Make the Tough Decision
Now, decide who you're going to hire! Remember some key points:

  • Your boss is looking to you to hire a competent, successful employee that can grow with the company. Cost is not a big concern.
  • Your technology is ever-adapting, and you need someone who has the wit to pick up the new systems and the personality to adapt with a smile and stay loyal.
  • Since your organization is largely made of account managers, you need someone who can get along with these individuals and do their job well.

As you can see, no candidate available is perfect for the job. It's up to you to choose best person for the job. Vote below, and provide reasoning for your choice in the comments! Or, feel free to continue the conversation on Twitter with me by messaging @breinholz.