When the Dream Job Becomes a Nightmare

Yes, it can happen, even when a situation looks like a great fit. Here's how to probe deeper during the interiew process

Dear Liz,

I am in a very unexpected job situation. Seven years after completing my MBA and working in product management positions in several good companies, I made a plan to pursue my dream job, managing products in the natural-foods industry. After a six-month, stealth job search I landed a tremendous position with a well-regarded, fast-growing natural foods company and was in heaven for the first several weeks.

After that, my dream job began to fall apart. Five months into the role, it is clear that I need to make another move. The company is completely disorganized, there is no desire to create a business infrastructure, and as a result nothing that we commit to as an organization happens on time. Our customers are wholesalers who are losing patience with our dismal track record for shipments, billing, marketing support, and everything else. The CEO is a visionary type who has an idea every three minutes but executes on nothing, and his leadership team, including my boss, is too fearful to speak up. It's a very bad situation, and I fear that sticking around here may tarnish my reputation among people who know the industry, and drive me insane.

I will start a new job hunt after the holidays, but I want to get some learning out of this situation. On paper, this looked like the best job a person at my career stage could hope for, and I was over the moon to get the role. Now I am sorry I ever got involved. What did I miss, and what should I be looking for next time around?


Dear Paul,

I'm sorry that this lesson has been so costly and stressful for you. It is normal for what looks like a dream job at the outset to settle into merely an excellent, very good, or not-terrible job over time. But it's a shock and a huge disappointment to find that your dream job is a nightmare.

As you head into the job market again in 2008, you could think about your evaluation of a prospective employer this way: as a staircase. At the lowest step, you can learn plenty of key facts about the employer's market position, its customer relationships, history, and leadership team, without ever speaking to a company representative. Obviously, if the company's Web site were an unintelligible mess or its board members were under investigation, you'd turn your attention elsewhere. But so much of what's important is not available to online researchers, as diligent as they may be. There's only so much you can learn about an enterprise at that first stage of the process.

That's why, once you get into the organization for a face-to-face interview, you need to expand your line of questioning and your own observations to include some second-step issues. In your case, to avoid another we-don't-do-infrastructure environment, you could ask probing questions about the sales order process, the inventory allocation process, and whatever other processes you're interested in to see how the prospective employer is situated back-office-wise.

The good news is, once you've been bitten by this particular snake (We're inventors! We're creative! We make it up as we go along!) you aren't likely let it happen again. But there are other snakes out there—companies that don't communicate across functions, companies that work their employees to death and keep them in the dark, among plenty of other venomous or constricting species.

It pays to ask more in-depth questions as you move through the hiring process—and to talk to people who work at the company now but who aren't involved in the hiring process (you can find them and reach them via LinkedIn) or who used to work there, and to any customers and/or suppliers you can locate.

Here's a quick stair-step model for you to keep in mind as you go:

Step 1: Information you can acquire on your own, before an interview

What's the industry? What size is the company? What is its competitive position (market-leading, plucky upstart)? How long has it been in business? Who's the CEO, who's on the leadership team? How long has the team been in place? What is the recent company news, industry news, or trends? What about CEO or other leaders' remarks in industry publications, at conferences, or in the business press? Have there been recent high-level leadership appointments?

Step 2: Information about the internal operations and organizational structure/processes that you can acquire on your first round of interviews

What level of business process is in place? What systems are used, and for how long, how successfully? How does marketing/distribution/product development work? What major challenges exist in the area you'd be working in? How does the organization communicate—what combination of face-to-face, electronic, conference calls, etc? How hierarchical vs. free-form is the organization? How are teams organized? How is success measured internally? What major "people" issues is the organization facing? What is a career path likely to look like if you accept the position?

Step 3: Information about the personalities and cultural norms that you can acquire on second, third, and fourth interviews and by talking to outsiders familiar with the company

Who runs the show, and how does s/he do it? What is the CEO's leadership style, and how does that affect the rest of the organization? Who are the movers and shakers in the group, and how do they operate? What does the organization value in its team members? Which behaviors (e.g. analytical rigor on one end of the scale, or brilliant showmanship with customers on the other) get rewarded and which get punished? Who thrives here and who shrivels? Which types of employees stay, and which leave? What is the one inviolable cultural rule for the organization (e.g. "Don't say anything stupid in front of the CEO" or "Don't let a customer down")? What are the stories that best describe how the organization ticks?

Next time around, Paul, you'll do even more due diligence than you did last time. You'll analyze every interview conversation and post-interview e-mail exchange to pick up on clues that those interactions may hold about what working for the organization would be like day-to-day. None of us has a crystal ball to see everything we might wish to see inside an organization before coming on board, but you're not likely to have such an unfortunate surprise again.

And remember this, Paul: many of the roles that become dream jobs for us over time don't look like dream jobs on paper. In the right organization, you can build a perfectly ordinary role into a dream job by showing what you can accomplish, building relationships, and helping to move the organization in the direction it needs to go. Best of luck to you.



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