Learjet flight crew reported a heading deviation on the skyline 6 departure from oak.

Attributes
ACN	1448430
Time
Date	201705
Local Time Of Day	1201-1800
Place
Locale Reference	OAK.Airport
State Reference	CA
Environment
Flight Conditions	VMC
Light	Daylight
Aircraft 1
Make Model Name	Bombardier Learjet Undifferentiated or Other Model
Operating Under FAR Part	Part 91
Flight Phase	Initial Climb
Route In Use	Vectors SID SKYLINE 6
Flight Plan	IFR
Person 1
Function	Captain Pilot Flying
Qualification	Flight Crew Air Transport Pilot (ATP) Flight Crew Multiengine Flight Crew Flight Engineer Flight Crew Flight Instructor Flight Crew Instrument
Experience	Flight Crew Last 90 Days 234 Flight Crew Total 24000 Flight Crew Type 3500
Person 2
Function	Pilot Not Flying First Officer
Qualification	Flight Crew Commercial Flight Crew Instrument Flight Crew Multiengine
Experience	Flight Crew Last 90 Days 75 Flight Crew Total 514 Flight Crew Type 151
Events
Anomaly	Deviation - Altitude Overshoot Deviation - Procedural Clearance Deviation - Track / Heading All Types

Narrative:

Departed oak on an IFR flight plan which included the skyline six departure procedure. My first officer was a low time pilot with 500 hrs total time and 125 hrs in the learjet. He read the departure procedure to me which was fly heading 278 to 3;000 then left heading 200 to intercept the 135 radial from pye. He failed to read the departure route description which was to climb on heading 278 vectors to pye 135; cross 4 DME northwest of oak at or below 2;000 and above 1;400. I did not verify the routing on my ipad and assumed what he told me was correct. After turning to 200 at 3;000 feet; ATC shortly thereafter vectored me back to heading 270. We were then vectored and assigned higher altitudes. We were assigned FL190 and then ATC said we needed to copy a phone number for norcal. In the process of copying the phone number we flew through FL190 by about 1;500 feet.several factors contributed to these deviations:1. It was a long day and by the time we departed oak we had been up for 12 hours. I discovered that my first officer did not get any sleep the night before.2. My first officer is very inexperienced and has not had much instrument procedure time other than what he received to get his ratings.3. Captain failed to verify departure procedure with first officer.4. Captain tried to multi-task by flying the airplane and copying a phone number from ATC.5. Captain failed to use appropriate automation to lighten the work load i.e. Altitude capture feature of the autopilot.I feel fatigue; an inexperienced first officer; not verifying departure procedure with first officer; and not using auto flight features of the learjet all contributed to these deviations. To correct some situations; I feel it is necessary to fly a high performance aircraft with a more experienced crew member. Use crew resource management techniques to verify that both crew members are in agreement with procedures and to use aircraft automation to lighten the work load in high workload environments.

Original NASA ASRS Text

Title: Learjet flight crew reported a heading deviation on the SKYLINE 6 Departure from OAK.

Narrative: Departed OAK on an IFR flight plan which included the Skyline Six departure procedure. My First Officer was a low time pilot with 500 hrs total time and 125 hrs in the Learjet. He read the departure procedure to me which was fly heading 278 to 3;000 then left heading 200 to intercept the 135 radial from PYE. He failed to read the departure route description which was to climb on heading 278 vectors to PYE 135; cross 4 DME northwest of OAK at or below 2;000 and above 1;400. I did not verify the routing on my iPad and assumed what he told me was correct. After turning to 200 at 3;000 feet; ATC shortly thereafter vectored me back to heading 270. We were then vectored and assigned higher altitudes. We were assigned FL190 and then ATC said we needed to copy a phone number for NORCAL. In the process of copying the phone number we flew through FL190 by about 1;500 feet.Several factors contributed to these deviations:1. It was a long day and by the time we departed OAK we had been up for 12 hours. I discovered that my First Officer did not get any sleep the night before.2. My First Officer is very inexperienced and has not had much instrument procedure time other than what he received to get his ratings.3. Captain failed to verify departure procedure with FO.4. Captain tried to multi-task by flying the airplane and copying a phone number from ATC.5. Captain failed to use appropriate automation to lighten the work load i.e. Altitude Capture feature of the autopilot.I feel fatigue; an inexperienced FO; not verifying departure procedure with FO; and not using auto flight features of the Learjet all contributed to these deviations. To correct some situations; I feel it is necessary to fly a high performance aircraft with a more experienced crew member. Use Crew Resource Management techniques to verify that both crew members are in agreement with procedures and to use aircraft automation to lighten the work load in high workload environments.

Data retrieved from NASA's ASRS site and automatically converted to unabbreviated mixed upper/lowercase text. This report is for informational purposes with no guarantee of accuracy. See NASA's ASRS site for official report.