Questions for the Next Gig

I was asked to provide career coaching feedback on a new employment opportunity, so I worked up these questions. These questions are equally applicable to a startup or other business opportunity, with suitable modifications around manager / company / product or services .

Ask the questions before you become emotionally invested in the opportunity. Once you get past that line, your emotional investment will color or skew your perceptions to the point you will not be able to be objective about the answers.

Use as many objective, fact-based data points as possible, and keep a log or spreadsheet that rates and weights the answers.

Questions #1 – #3 are absolute show stoppers.

It can be possible to overcome #4 if you can see a clear path to obtaining the necessary skills, etc. Most entrepreneurs get to where they end up by answering “Yes, I can do that,” to every challenge and figuring it out as they go along. That approach does not disqualify you for opportunities, but you need to be honest about how that changes your risk profile.

The answers will never come back all positive, but the goal is to have the majority of the answers to questions 5-11 come back positive. Some negative responses, such as those around customers, products and services, etc., may provide leverage points for negotiations.

Questions for you to ask:

  1. What are your life goals? What are the most important, top-three things on your list of life priorities? Would this role advance you towards those goals? If so, proceed.
  2. Will this opportunity be a positive or negative impact on your marriage/primary relationship(s)? If positive, proceed.
  3. Other than money, what intrinsic and extrinsic rewards does this role provide you? Are those rewards sustainable over the mid- to long-term? Do those rewards provide for most of what you need? If so, proceed.
  4. Are you qualified for this position? That means, do you have the applicable skills, experience, motivation, network, health, outlook and capabilities to be successful in this role? Be honest. If yes, proceed.
  5. What will your life be like on a Tuesday morning four years from now if you take this opportunity? What will an average day be like? Does that sound like a day you want to be living then? If so, proceed.
  6. What is this market segment? What is its current size in number of customers and total sales? What size is your territory or accessible market (the market you can reach with your available resources)? Is it growing or shrinking in sales and customers? How many viable customers exist in your territory or accessible market? Are there more and more or less and less? Is this a growing, vital market, a “walking dead” market or a shrinking, dying market? Do the answers to these questions add up to a positive opportunity? If so, proceed.
  7. What is the competitive position of the company? Is it a market leader? Is it growing in sales? Is it financially successful? How many employees does it have? What do former and current employees say about the company? What do current, former and prospective customers say about the company? Do the answers to these questions add up to a positive opportunity? If so, proceed.
  8. What is it like working for your prospective new manager? What do former and current employees have to say about him/her? How secure is he/her in his position? Is he/she working under “golden handcuffs” after an acquisition or other employment agreement? If so, how much longer is he/she contractually obligated to work for the company? What happens if he/she leaves? What are his/her sales targets? Are those targets part of the acquisition or employment contract? Are those goals achievable? Do the answers to these questions add up to a positive opportunity? If so, proceed.
  9. What are the products or services? How many products or services will you sell? Will you be a “one trick pony” or have a range of products or services that can meet the needs of a variety of customers and markets? Does the product or services line put you at risk for a particular segment of the economy? What is the reputation of the products or services in the marketplace with customers? What do past, current and prospective customers have to say about the products or services? For customers who no longer buy the products or services, why did they stop? For customers who don’t buy the products or services, why don’t they buy them? Is it possible to overcome those objections? Is there enough margin and commission in the product or services line to add up to a decent life and make up for the downsides of the role? Do the answers to these questions add up to a positive opportunity? If so, proceed.
  10. What do past, current and prospective customers have to say about this opportunity? Talk to ten to 20 past, current and prospective customers of the products or services. Ask them straight up about the company, products or services and if they would take a job with the company. Do the answers to these questions add up to a positive opportunity? If so, proceed.
  11. The last thing to worry about is the money. If the answers to #1, #2 and #3 are good, then the money is not a very big consideration. Money is the worst reason to take a job, since the motivation of money fades very quickly. You’ll be a lot happier if you concentrate on the other things the job brings other than money. If you like the people you work with and your customers, then your life will be happy. No matter how much they pay you, it will never make up for bad people. Will the money cover what you need it to cover and provide a little extra for some things you’d like to do? If so, proceed.

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