Why a safe candidate may in fact carry the most risk

August 13, 2013 Leave a comment

We are silent witnesses in an executive meeting of a very real software company.

“Need a new CTO”.   Got it.

“He / she must be capable of driving innovation and disruptive change”.   Makes perfect sense.

“He / she should fit neatly in our culture”.   Got it but with reservations.  More on that later.

“We want someone who has been there  / done that”.  Agreed – to a point.  More on that also later.

“Let’s hire an executive search firm.  We need someone fairly quickly”.    That’s where “the safe candidate” trap presents itself.

Why don’t we define Innovation first?  What is Innovation?

The definition I like (and it certainly stood the test of time) is the one which helps illuminate why many executive searches for a CTO do not produce the right CTO.   I speak from experience as a CTO-for-hire.  Many of my clients are technology companies who hired the wrong CTO or realized the current CTO cannot deliver an effective fusion of “people, process, and technology” to support the next wave of business growth.

Innovation is the ability to see the future and define a practical path towards it, where practical path means building a world class organization (people), doing things right the first time (process), and using technology in a truly transformative manner (technology).

Highly innovative CTOs live and breath the above definition.   Highly innovative CTOs also realize there is no innovation without disruption.   Disruption is healthy but presents many challenges.  One very common challenge is how existing business unit leaders – and P&L owners – may see innovation (and diversion of resources)  as a risk in achieving revenue and profitability objectives.   Planning for disruption and building a culture around it is the only way to nurture and foster innovation.   

There is an rarely spoken term used to describe candidates during the executive search process:  a safe candidate. Safe candidates are typically from the same industry / possibly a competitor with the same revenue, held the same role for at least 5-6 years, similar revenue / profit, led an organization of a similar size, and sponsored and led very similar initiatives.

Safe candidates are seemingly perfect.  Yet they are not.

Imagine running one of the world’s largest airlines.  It’s an incredibly complex business with an immense investment in technology and systems to run the business effectively and in a competitive manner.  You are the CEO and you need a new CIO (or CTO).   Do you look for a CIO (or CTO) from another airline?

In 2000, Delta Airlines hired Charles Feld, a former CIO at Frito Lay, to lead Delta Airlines technology organization.  Charles Feld was instrumental in accelerating introduction of many technology enabled, innovative solutions at Delta Airlines.   Does it make sense to hire someone from the leading manufacturer of salty snacks to lead a technology organization of a large airline?   It makes perfect sense because innovation gene is highly portable.

It’s tempting to hire someone who is a safe candidate.  If the job description calls for someone who can clearly demonstrate innovation gene,  identifying and selecting the right candidate – not just a safe candidate – becomes much harder.   The outcome however will be very much worth it.

This company will not have to hire me to fix things later.

There is of course much more to hiring the right CTO.   The right, highly innovative CTO may unexpectedly come from a completely different company with a completely different background.   It literally pays to keep this in mind.

To a CTO: “you are now responsible for alignment”. What to do next …

It’s not uncommon for a new CTO to receive a new mission to align the evolution of technology roadmap with the  evolution of the company’s business.

So the immediate questions in the new CTO’s mind are …

– Is it a minor problem which requires a corrective action?

– Is it a fairly difficult problem to solve?   Probably – because clearly someone very senior with an ability to directly control or influence the outcome would be needed to engage and get it done

– Or perhaps this could be a symptom of a larger problem?    Very likely.

As companies grow and become more complex, the lack of alignment becomes more evident – just like the cars we drive at some point need wheel alignment.    This is not an automotive blog but it’s helpful to mention that wheel alignment is a very complex procedure of adjusting multiple suspension components to achieve desired driving characteristics.

Software companies also consist of major components.   It’s important to recognize that the CTO cannot align all components.   The CTO can only influence the alignment process by asking the right questions.  Some may not be very popular.    More on asking unpopular questions in a moment.   But then again – wheel alignment is not an easy procedure either.

The major components of a software company:

–  Turning ideas into product ideas (product management)
–  Turning product ideas into real products (engineering)
–  Evangelizing products in target markets and customer  segments (marketing / product marketing)
–  Selling products (sales)
–  Servicing customers (professional services and support)
–  Supporting the company operations (HR, administrative)

That’s it.    Only a few components – or functional areas – to align.

Alignment is first and foremost a leadership challenge, not a process or technology challenge.   And that’s why alignment starts with the most senior leader in the company:  the CEO.   The CEO needs to set the tone and adjust the measures of success of each senior leader in such a way that their success cannot be achieved without working effectively with other leaders. Only then alignment can become what I believe is the right way to recognize alignment:  continuous, effective and never mentioned again as a separate initiative.

I will share an experience that many readers can relate to.   It’s a launch of a new product with many problems which highlight (an extreme …) lack of alignment throughout the company.   For each problem – I will also include questions – perhaps unpopular yet very necessary – the CTO can ask.

The new product was intended for a new market segment outside of North America.

Problems and questions that were never asked at the right time:

– Resellers were not trained to sell the new product, leading to significantly lower revenue expectations.   “What is the plan to audit existing resellers, select resellers interested in selling this product?  When do we start training?  Where are the training materials?”

– Direct sales force did not receive any incentives to sell a new product.   “What changes do we have to consider in the sales compensation model to fuel adoption of the new product?”

– First few customers did not like certain capabilities.  Formal launch had to be delayed.  “How can the product management team incorporate an early adoption cycle in the product launch plan?  How can engineering team respond to problems or feedback points identified during the early adoption cycle?”

– The customer support team did not hire technical support engineers in the target country who could speak 3 additional languages.   “What are the customer support requirements?  What is the hiring plan?”

– The budget for launching the new product was not accurate.   Sales compensation changes were not included.   Reseller training costs were also not included.  “Did we recognize all the costs of launching the new product?  Who maintains an accurate financial model which incorporates the financial impact of all decisions and changes?”

– The company did not have an Integrated Product Launch (IPL) process which provided 100% visibility to all cross functional activities, milestones, and dependencies.   While the engineering team was busy building a new product, the customer support team wasn’t ready to support the new product on day one.    “Do we have a process to manage all activities, milestones,  and dependencies?  Who owns it?  Does this person have the authority?”

The last point is one I cannot say enough about.   Alignment can never be achieved without a set of real time measures, fully supported by all components of the organizations – ready to adjust in real time when needed.    That’s when alignment becomes a non-event: organic, continuous, and effective.   And that’s where any software company wants to be.   Great CTOs believe and practice alignment every day.

The war for talent – Part 3: “Where are all the great candidates?”

It’s 9am.

This is my first meeting with client’s engineering managers.  The objective is simple (CEO’s exact words): “I want to see a world class software engineering team generate world class return on investment and fulfill the promise that technology is an enabler of sustained competitive advantage.  Do whatever it takes.  Nothing and no one is sacred”.

I interviewed all senior engineers first – not managers, to the surprise of many managers.   Common theme from these interviews:

– “Almost every new hire is somewhat average;  no passion or drive.   The most recent hire did not care much about a broken build until we reminded this person how a broken build defeats the work of everyone else”.

The Interviews with all managers were more revealing.  Common theme from manager interviews:

– “Our recruiters seem to present candidates that are good, but not exceptional.   We don’t have a choice but to hire one of these candidates”.

The interviews with recruiters were more revealing – again.  Common themes from recruiter interviews:

– “We get very uninspiring job descriptions from hiring managers.  These job descriptions do not resonate well with exceptional candidates”.

– “Compensation is below market.   It’s too hard to obtain an exception for a higher compensation.  We stopped trying.”

– “Many hiring managers do not respond quickly and better candidates are hired by another company.”

– “We rarely receive feedback why certain candidates have been rejected.  Very difficult to improve the recruiting process.”

What’s not  very difficult to see is the root cause of what happened to my client’s software engineering organization over time.  The managers forgot that their first and foremost responsibility is to the organization:  attract, recruit, hire, and retain the very best.

I asked every manager to watch a movie called “Miracle”.  It’s a true story of Herb Brooks (played by Kurt Russell), the head coach of  the U.S. Olympic hockey team in 1980.  The U.S. Olympic hockey team played the against the heavily favored USSR team and won.

This movie highlights what every manager must live and breathe:  never give up the responsibility for building, managing, and improving a great team.   It’s a difficult, often hard, but a very rewarding process.

I asked every recruiter to stop reviewing resumes and made every manager responsible for the initial review and subsequent phone screen.   The results:

– 3 managers out of 6 did not see value in this process and told me that that’s what recruiters are for.   I asked them to consider a very simple fact.   If someone cannot identify a terrific candidate from a stack of resumes, why should this person be given the responsibility to manage, coach, and mentor any hire?

– 2 managers agreed and became better managers.  1 manager left within one week.

– The other 3 managers fell in love with the new process, despite the additional workload.   The new process allowed them to build very close relationships with recruiters who began to receive detailed feedback about each candidate.

In addition, more changes have been made:

– I asked everyone to review all previously rejected resumes – over 1,200 – and look for evidence of three critical items:  ability to learn, ability to blossom in adverse situation, and ability to solve problems while never giving up.

– This process produced 60 potential candidates.   7 were eventually hired and quickly became highly respected members of the team.

– Compensation inequities have been addressed within one budget cycle.

After 12 months, I provided a report card to the CEO with 4 metrics:

– “No more complaints from the management team that there are no great candidates’

– “Employee participation in the HR survey increased from 55% to 87%.   The management team in a 360 degree survey received B+.”

– “The last 3 major releases had a total of 3 regression issues vs 213 regression issues same time last year”.

– “Customer survey – NPS or Net Promoter Score – also showed substantial improvement.”

“Where are all the great candidates” is the wrong question.   Are your managers engaged 150% to attract, recruit, hire, and retain the very best?

The war for talent – Part 2: “Are you the same person I hired?”

This blog post has been long overdue.

While hiring a senior candidate, it’s not uncommon to spend 4-6 months searching, attracting, recruiting, negotiating, and finally witnessing the perfect and long awaited new hire arrive.

For you, a very senior executive, the time invested to learn about the new hire during the recruiting process wasn’t insignificant. In addition, you asked other executives and members of senior staff to interview this candidate. The decision was almost unanimous. Other than one concern, everyone cheerfully suggested to proceed with an offer.

The first 90-120 days passed quickly.

Yet something isn’t right. The new senior hire isn’t enjoying the kind of support throughout the organization you had expected. Critical initiatives being led by this individual aren’t advancing beyond the polite discussion stage. In other words, very few see value in working with this individual.

What happened? All the right questions have been asked during the recruiting process. 360 degree evaluation became 720 degree evaluation with multiple interviews from other executives and members of senior staff. Clearly, the due diligence did not produce desired results.

“Things would be much simpler if everyone listened to me and did exactly what I prescribed”

Not every candidate or later employee will say it. Some do and can never take their words back. Some are sophisticated enough not to say the above words, but practice these words in action every day.

In my earlier post, I’ve written about the need to put every candidate in the position of extreme hardship and work with him / her while observing whether he / she can …

– Build a shared agenda in a difficult situation? Or – will he/ she simply prescribe what to do and become frustrated if no one listens?

– Realize that in difficult times he / she needs the support of the direct as well as indirect team members more than ever?

– Recognize that no amount of dictating from a throne will convince an all-volunteer army to go to battle that no one understands

– Recall reading a book titled  “Crucial Conversations: Tools for Talking When Stakes Are High” by Kerry Patterson

“I accomplished amazing things in my past. I will continue to remind you of that every chance I get”.

At some point, the above words – or words phrased differently but with the same meaning and intent – will also begin surface from the candidate that isn’t meeting high expectations. How does someone, clearly capable and smart make this mistake? They forgot that prior medals mean very little when joining a new position with much to accomplish and high expectations.

It’s essential to learn about the business first, win respect from members of senior staff, and only then lead while using prior accomplishments as lessons learned.

Imagine someone who is a very experienced plumber, working with mainly builders who construct single family houses.

During the interview, ask the candidate to consider plumbing design issues on an aircraft carrier where 5,000 people work together as a team in three shifts around the clock. The right candidate will start with many questions before providing a meaningful answer. The wrong candidate will suggest a conclusion far too early.

“I don’t know the answer but want you to accept my answer even if it shows lack of clarity in understanding and next steps”

Once the seemingly perfect candidate crosses this boundary, their success is no longer possible. The overwhelming desire to provide an answer instead of finding an answer together with his / her team or other colleagues will lead to organizational equivalent of alienation. Very few will follow a poorly thought path to success and elect to work on other urgent, but more clearly defined, objectives.

This is why placing a candidate in the position of extreme hardship during an interview will easily reveal whether the candidate can find an answer together with his / her team. It’s impossible to design an effective sanitation system for 5,000 people on a vessel without asking the right questions from other contributors.

Jeff Bezos said, “you earn reputation by trying to do hard things well”.

Make your best candidate earn their reputation by asking them to do extremely hard things well during an interview.

Still reluctant to place senior candidate in a difficult situation during the interview?

“Somebody once said that in looking for people to hire, you look for three qualities: integrity, intelligence, and energy,” says Buffett. “And if they don’t have the first, the other two will kill you.”

Someone’s integrity will always shine in a difficult situation.

The war for talent: what to ask in the final battle before making an offer

March 17, 2013 1 comment

The commonly described Dot Com Bubble finally burst in late 1990’s.

One of the unintended consequences of this inevitable milestone was the beginning of a talent shortage.    I was fairly certain that in 10 years the talent shortage would be apparent.   I was wrong.   The talent shortage is now more severe than ever.

How did the talent shortage become so severe?

– The recession which followed caused many great software engineers to leave the industry or become underemployed long enough to be considered no longer top talent

– Many companies aggressively shifted software engineering activities to lower cost countries, leading to (and this is the real reason why we find ourselves in this position …)

– Amazing problems solvers with a passion to build something new and exciting decided to bypass software engineering and elected to pursue other professions.   Why become a software engineer if my favorite company where I’d like to work is in the news shifting great jobs (out of sheer necessity to survive, however …) to another country?

Those who remained in software engineering and continued to advance their craft became the smaller community of talent that is subject to many discussions at the present time, or “the war for talent”.

Glenn Kelman, the CEO of Redfin could not have described the war for talent in his recent blog entry, titled “Searching for Beasts in Silicon Valley’s War for Talent”.

Jeff Bezos, the CEO of Amazon, once said (and it became one of my favorite quotes), “You earn your reputation by trying to do hard things well”.

Returning to Glenn Kelman, when evaluating a new hire the question Glenn wants answered is, “When did he / she do something hard?”.

Before making an offer to a great candidate, learning how he / she succeeded while attempting to do something very difficult will be perhaps the best indicator if the offer should be extended.

Some of my best hires emerged from a conversation during an interview where I described a problem impossible to solve in 2 hours and nevertheless asked the candidate to begin thinking about the solution together with me.    These hires all exhibited the basic traits of a great hire:  tough, resourceful, and relentless problem solvers.

Two perfect offers: how do you choose or why organizational courage matters

February 9, 2013 1 comment

Your colleagues call you the very best software engineer they ever worked with.  Your relationship with the current manager could not be better.   But you are not growing as a professional, or perhaps the reasons why you want to explore new opportunities are simply private.

The interviews have been exhaustive but every company you spoke with is very interested in extending an offer.

Yet you are patient, because finding the right opportunity, the one that will proper your career forward, remains the most important goal.

Two companies are literally opening every door (and every window) for you.    You feel very comfortable and excited about joining either one.   Even the commute is the same.

As expected, two offers have arrived.  Both are very attractive.   How do you decide?    Simple – the company which exhibits and encourages ‘organizational courage’.   So how do you learn – as a brilliant software engineer – if the company does exhibit ‘organizational courage’ and why it’s even important?

Very few organizations exhibit what I call ‘organizational courage’.   It can only exist if the leadership team actively promotes and encourages ‘organizational courage’.

How do you find out if the company exhibits ‘organizational courage’ during the interview process? 

I hired an amazing software engineer some time ago.  “D” came to me 4 years later and resigned.   I understood.  “D”‘s new role would be more visible and a much better fit for “D”‘s career goals.   There was little I could to retain “D”.

Over lunch (the right way to do exit interviews), “D” smiled and told me how he evaluated my offer and the offer from another company.  I remembered that stressful week waiting for ‘D” to respond to my offer.    “Why did you accept my offer?”, I asked “D”.  ‘D” replied, “You were the only one who gave me an honest response to what happens if the product management team does not provide detailed specifications on time”.

“D” even recalled what I told him during the interview.  “Slow down the release process, do not code fictional functionality, and get detailed specifications – even if someone does not sleep for a couple of days.  Or – product managers and engineers enter one room and do not leave until everything is clear.   Again – no fictional functionality based on fictional requirements just to meet the release date”.

“D” said, “I knew that that’s the team culture I wanted to be a part of”.    Although “D” did not mention it by name, ‘organizational courage’ is an important element in evaluating several, seemingly perfect offers.

During the interview, ask probing questions to create your own understanding of whether the culture you may join exhibits ‘organizational courage’

– What happens if the release is late?  How do you perform lessons learned?  How do you apply lessons learned?

– What happens if the professional services team is very unhappy with the installation process, configuration capabilities, or error reporting?

– Is there a customer that is genuinely dissatisfied?   What are the root causes?  What are you doing about it?

– What is your track record making and executing difficult decisions – but for the right reasons?  Can you provide examples where the goal was not to reach a compromise but to deliver what the customer really needed to be successful?

Why it’s important to learn about ‘organizational courage’ during the interview process

Your career progression depends on it.

Why promoting ‘organizational courage’ makes perfect sense to any manager

“D” left my team but recommended his former co-worker, “J”, who turned out to be a terrific engineer.   Time from open requisition to hire to closed requisition:  6 days.    “J”‘s comments after spending the first week, “This is the best place I ever worked”.

2013 New Year Resolutions for all CTOs

December 31, 2012 Leave a comment

The most successful CTOs are managing champions of a process developing and executing technology strategy which helps deliver measurable and sustainable business results.

That’s the common wisdom.   I believe that exceptional CTOs are exceptional because they take this common wisdom even further:

“… deliver measurable business results which create a sustainable competitive advantage”.

It’s very comforting to see your closest competitor in the rear view mirror.  Yet the journey to this point in a company evolution is extremely difficult.

It does not have to be difficult.   The three elements of success – people, process, and technology – have not changed.  Exceptional CTOs know this very well.

My selected New Year resolutions for all CTOs in 2013 …


– Bring the question of strategic alignment into every conversation, even if someone else is responsible for executing other elements of company’s strategic and operating plan.   Does Sales organization have capacity to begin training well in advance of the launch date of a new, more complex solution offering?  Who is responsible for enabling Sales organization?  Is the Customer Support organization ready to accept the first call from a customer using the new major release?  Is the root cause decomposition process working?   Will it lead to a discovery of defect?  Or – a recognition that training was inadequate?

– You may build the best product.  But someone else may need your help to educate the Sales team.  Do not be afraid to bring it up and get on the road to educate the Sales team or even engage customers in the early stages of the sales process.


– Great teams are built and nurtured, not created.   Hire people who can demonstrate they subscribe to the mission and can work with others.  Great talent working alone does not contribute to the larger goal.   Get to know every engineer and treat each individual like they are the most important person.

– Tell your team on January 2 that you in fact work for them (instead of everyone working for you).  Your job is to establish clear objectives, enable everyone, remove barriers, and get out of the way.  This is the “right side up” organization – and it works.

– Great teams are quickly minimized by marginal managers.   Find a suitable opportunity for  them outside of your company.  Never transfer problems.   Do not be afraid of managing directly while finding a replacement.  Ask the most senior members of the team to participate in the interview process.

– Dedicate at least 50% of your time coaching the team.   Find a way to change the course of a meeting where the majority is trying to convince the minority why something may be impossible.   What if the minority is right?  What if something impossible is actually possible?   How do we – as a team – shift the dialog and determine one or more alternatives?

– Remind yourself every morning that listening is more important than talking

– Remind your team members that complex problems often require a collection of techniques in order to create a sustainable solution.  Excessive reliance on one process or technique often leads to failure

– If your team fails, immediately accept the failure for the team.  Then find the answer together


– Automate everything

– Bring focus on quality as early as possible in the design cycle.  If the functionality depends on correct database state after a series of updates, did anyone consider how to create an automated testing harness to generate several database states in order to test this functionality in the future?

– Over invest in the build / release engineering infrastructure

– Over emphasize defensive programming

– Over emphasize self educational error management, logging, and reporting approach;  ensure this is reflected in every engineering estimate

– Build and foster a culture where the value of finding and addressing the root cause is more important than who caused the problem

– Institute few metrics which are truly meaningful and highlight the performance of your organization.   One metric I ask my engineers to recognize in everything that they do:

“The root cause of every problem – no matter how complicated – must be identified in less than 60 minutes”

Imagine how a complex software product must be designed and engineered to meet this goal.

Adjust your rear view mirror and don’t stop in 2013 until every competitor is a distant fixture behind you and your team.

Happy holidays!

Categories: Software Engineering