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How to practically guarantee an offer to become the new CTO

Highly admired, rapidly growing technology company has been searching for a new CTO who would play a critical role in the company’s next growth cycle.

You – the reader – were selected as one of the top 10 candidates and later as one of the two final candidates.   However, the company decided to hire the other candidate.  Why?  The truth is – you will never know.   But with hopes to help anyone being considered for a senior technology leadership position, I wanted to provide more visibility about the reasons why a seemingly terrific candidate ultimately did not receive an offer.

The top 3 reasons why the offer has not been extended to you:

1.  You did not ask the right questions, in the right sequence.

2.  You did not explain correctly what you would doing next Monday in your new role as a CTO

3.  You did not exhibit enough evidence of being able to quickly win the respect of both technology organization and other executive peers.

You did not ask the right questions, in the right sequence.

The job of any CTO in a software company is not to manage technology but to ensure that technology strategy supports the economic goals of a business, or 100% alignment between different phases of growth and how technology must evolve to support each phase of growth, while thoughtfully recognizing that some key initiatives must be sponsored and financed well in advance.

You must learn as much as possible about the company’s business during the interview process – in the right sequence.

First – learn about the company from the CEO (not an exhaustive list):  roots, key evolution milestones leading to the present, broad market conditions, major competitors (VP of Sales will provide more details), capital structure, investor profiles, investor goals, and resulting financial targets as well as time constraints.   It may or may not be possible to grow revenues 200% in 3 years.   These matters will have a significant impact on you as a CTO.

Second – ask to speak with the CFO.   That’s right – the CFO.   He / she will share with you how the company’s strategic plans are translated into operational plans and budgets which include all other organizations.   Is there a history of underinvestment in the technology organization and product engineering?   What’s the budget history of the technology organization during the last 3-4 years?    Are you walking into an organization where you may not have the right budget to ensure the success of the product development goals?  Or – the organization is mature enough to have a meaningful discussion and agree with you (hopefully the very leader being sought), even at the price of reducing investment in other areas?

Third – speak to VP of HR.   Learn about the state of technology organization / ask for the organizational chart.  Compensation – is it competitive?  Are there any open requisitions?   Imagine a growing organization where a principal level engineer role has been open for 6 months.   Why couldn’t the right person be hired?    Start making notes.   Can you have a meaningful conversation with VP of HR if the compensation structure in the technology organization you are about to inherit and lead is inadequate and about to trigger significant attrition?

Fourth – speak with VP of Sales.    What are we selling?   How?   Are the customers happy?  If not – what are the reasons?   Is there a detailed win-loss analysis process?   Can you get a copy of the latest report?

Fifth – speak with VP of Marketing and Product Management.   Is the requirements management process rigorous?   Are the requirements collected from all the channels:   customers, competitive intelligence sources, professional services?   How are the requirements managed:  documents or requirements management system?  When was the last time the product roadmap was changed?   What were the reasons?   How did the organization respond to some critical features being delayed instead of accelerated?   Ask for the product roadmap presentation.

Sixth – speak with VP of Professional Services to validate the state of the customer.   Is the customer community satisfied?   What is the typical deployment process:  duration, complexity?   How can the product be improved to reduce the complexity of the customer deployment process?

By this point, you have demonstrated 2 items the executive team is looking for:

– Ability to learn about the business from key executive peers (something you will have to do anyway but the key is to demonstrate this competency during the interview process)
–  Ability to extract key insights which will allow you to begin thinking about aligning the goals of the technology organization with the goals of the company

You did not explain correctly what you would doing next Monday in your new role as a CTO

If someone interviewing you asks, “what would you do during the first 90 days”, chances are your value as a candidate has already eroded.   Do not wait until this question is asked.

Find the right moment to mention that you are already thinking about the plan.   But before proposing the plan, you need to learn a lot about the business, your own organization, as well as every other organization that are critical to your success.

What every CEO is looking for in a new CTO when the CTO discusses the 90-day plan:

– 0 – 30 days:  make no changes in the technology organization.   Engage every employee.  Listen & take notes.   Resist every temptation to make significant changes.   Focus on creating a culture of transparency and accountability.   Team superstars will respect you from day one.  Underperforms will realize that the time for a new job search has arrived.

– 31 – 60 days:   become a silent participant in all other meetings.   Attend sales pipeline reviews.   Attend customer account planning calls.   Learn the pain points in every other organization that may be addressed later by adjusting the product roadmap or simply correcting product functionality.   Win the respect of your executive peers by sharing their daily challenges.

– 61 – 90 days:   Invest time in creating a very clinical perspective on what you learned.   Present it to the executive team.   They may not even realize certain issues or opportunities exist.   Then begin working on a plan to meet current operational goals while introducing methodical changes to position the company for growth.   Present it to your own organization.   Do not hold back any information.   Your commitment to transparency and clear goals will be the reason why everyone will accept you as the new leader.

You did not exhibit enough evidence of being able to quickly win the respect of both technology organization and other executive peers

The best part about item 3:   if you have done well with items 1 and 2, this one becomes a non event.  You have already demonstrated your ability to win the respect of everyone you will be closely working with.

If you act as a CTO while being interviewed for a CTO role, the offer to become the new CTO will be practically guaranteed.


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  1. December 11, 2015 at 4:53 pm

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